


Nine Steps Out Of The Friendzone

by Kitmistry



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Bartender Dean Winchester, Dean/Cas Pinefest 2019, Fake/Pretend Relationship, Fluff and Humor, Friends to Lovers, Love Confessions, Love Triangles, M/M, Misunderstandings, POV Castiel (Supernatural), Pining, Pining Dean Winchester, Romance
Language: English
Status: Completed
Published: 2019-02-25
Updated: 2019-02-25
Packaged: 2019-11-01 18:41:16
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 9
Words: 40,333
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17872706
Author URL: https://archiveofourown.org/users/Kitmistry/pseuds/Kitmistry
Summary: Getting the man of your dreams is as simple as that!The article promised a foolproof plan to the love of his life and Castiel was desperate enough to try it. The days Michael ignored him were about to be over.With the help of his newly appointed wingman, one Dean Winchester, Castiel was ready to get out of his comfort zone and reach for the stars. As he and Dean spent more time together, though, and got to know each other, Castiel had to admit that his plan had one major flaw: what if he didn’t want to go through with it after all?





	1. Step 1: The decision

**Author's Note:**

> Here it is! My first fic and first time participating in this challenge. A lot to be excited about.
> 
> A huge thank you to [ mittens ](http://mittensmorgul.tumblr.com/) for being my beta and making this readable. I'm forever grateful to you.  
> And the biggest thank you and all my love to my lovely artist [ dmsilvisart ](https://dmsilvisart.tumblr.com/) who created all the lovely illustrations for the story. [ Go and giver her all your love, too. ](https://dmsilvisart.tumblr.com/post/183047049398/getting-the-man-of-your-dreams-is-as-simple-as)

 

_**friendzone:** _ _[n]/frend.zoʊn/ the state of being friends with someone when you would prefer a romantic or sexual relationship with them_

 

 

The sound of the rain tapping against the windows had almost lulled Castiel to sleep and the dim yellow lights they used at the office – Gabriel always described them as warm and inviting but still a little mysterious – were not helping him. Mr. Parker and the former Mrs. Parker had spent the last few months in and out of courts trying to get as much of their shared assets as each of them could, but everything had finally ended, and the final signatures were currently being signed. Just a few more minutes and Castiel would be free. The clock couldn’t tick away fast enough.

Castiel loved his job but divorces, and especially as messy as this one had been, were the type of cases he avoided like the plague. Gabriel had insisted that Castiel help Anna though, since it was her first case with their firm, and that’s why he was currently bored out of his mind. A soft kick under the table brought him back to focus, and he turned to Anna who was raising her eyebrows at him. Everything was finished. The former couple exchanged a tight smile and a nod, the lawyers shook each other’s hands, and everyone went on their way.

Meg looked up from the magazine she was reading as Castiel approached her desk and tilted her head to the side offering him a smirk. Some day, Meg Masters would start acting like an assistant should, but today was not that day. “Well you look like you just had a nap in there.”

“You know I didn’t,” Castiel said but ran his fingers through his hair in a vain attempt to keep it looking presentable. Even without a mirror he knew he failed miserably; his hair had a mind of its own, and he had to accept that. “But I spent half the meeting spaced out.”

Something behind Castiel caught Meg’s attention, her eyes focusing a little above his right shoulder, but before he could turn and look a hand landed on said shoulder and squeezed. “Great job Cassie. I knew I could rely on you to keep an eye on Anna.”

Shurley & Laufeyson was not the first law firm Castiel had worked for, but it was definitely the most casual one. Charles Shurley and Gabriel Laufeyson both insisted that their employees refer to them by their first names and promoted a very friendly and relaxed environment for their associates. _We are a family before we are a company,_ was their motto for as long as Castiel had worked for them, which was six years and counting.

“Gabriel,” Castiel said, smiling at the shorter man, “Anna did most of the work, I was just there to help and encourage her. I think she is ready for more responsibilities.”

“Yeah, well, we’ll see about that.” Gabriel took a pink box he had been holding behind his back with the hand not resting on Castiel’s shoulder and placed it on Meg’s desk. “Donuts. On me. It’s my birthday today.”

Using her pen to lift the cover, Meg peeked inside. After she was satisfied with the contents of the box, she turned to Gabriel. “Happy birthday. I would have never known it was today. All the garlands in the kitchen and the emails you’ve been sending all week did not get their message across.”

“Happy birthday, Gabriel,” Castiel cut her off, standing in front of her to hide her from their boss. “I wish you all the best.” He extended his hand out to Gabriel but instead found himself being squeezed in a deathly hug. All things considered, Castiel should have seen it coming. One couldn't talk with Gabriel about personal matters without ending up engulfed in a hug.

“Thank you, Cassie. And no more formalities with me, I thought we talked about this, we are bros.” Gabriel pulled back and punched Castiel playfully on the shoulder. “So what do the two of you say? I got Chuck to throw me a surprise party tonight, are you coming? It’s at the Roadhouse.”

“I’d love to,” Meg said, and Gabriel grinned brightly at her. “But I have an appointment to wax my mustache.”

The glint in her eye had Castiel worried for what she would say next. Against all his prayers and all the warnings Castiel sent Meg’s way through his eyes, the topic was not dropped.

“You don’t have a mustache,” Gabriel said confused.

Meg leaned with her elbows on her desk and rested her chin on her hands, giving them a sweet smile that promised to put Castiel’s career in jeopardy. “Because I get it waxed. I can give you the card from the place I go to in case you ever decide to get rid of that rat hanging from your upper lip.”

Wonderful. Castiel could always rely on Meg and her sharp tongue to make his life difficult.

“What rat?” Gabriel asked.

“That straight-out-of-a-spanish-porn-parody mustache situation you have going on,” Meg answered, using her finger to make a circle in the air and if a hole opened up right then and there, Castiel would’ve thrown himself inside and wished it was deep enough to reach the other side of the Earth. Also he would have really liked it if Meg could shut up.

With his right hand, Gabriel touched his mustache self-consciously and after a minute he burst out laughing. “You’re joking,” he said, pointing an accusatory finger at Meg who just laughed right along with him. Crisis averted, for now. “Cassie, I’ll see you tonight. Oh, and don’t worry if you didn’t have time to get me a gift, you can buy one tomorrow.”

As Gabriel walked away, Castiel turned to Meg, ready to chastise her for once again being rude to the man who could fire them both on a whim - which happened infuriatingly often - but she pushed herself off her chair and leaned over her desk until their noses were almost touching. “You are so going to become partner.”

Castiel stared at her in confusion. That was not the topic he was about to discuss. “Partner? I’m just happy he didn’t kick us both out with how you talked to him. _Again_.”

“Relax, Clarence. Gabe and I are just joking. But you-” she pressed her finger against his shoulder blade until Castiel was sure her nail would leave a mark on his skin, “are his bro. I’m telling you, the promotion is dangling right in front of us. You get the big office and the six figure salary, and I get the raise I deserve and my own parking space.”

“Meg you know I don’t care about becoming partner,” Castiel sighed as he took a step back and straightened his suit and tie. He didn’t comment on the nickname, Meg had been calling him Clarence since the day she had shown up at his office for her interview. To this day Castiel wasn’t sure how he’d been convinced to hire her -could be magic or it could be she’d decided by herself she started on Monday - but he’d never regretted it. She was the best personal assistant he’d ever had, and she had the extremely useful talent of uncovering all the skeletons their opposing side had to hide. It wasn’t always a lawful skill, as the many nights Castiel had spent playing lookout while Meg went through people’s desks and wardrobes could attest to, but a useful skill nonetheless.

Meg tilted her head to the side so she could look past him and then narrowed her eyes at someone walking behind Castiel. He didn’t have to turn to see who it was, he could tell just from the way her lip curled up on one side. “You don’t care about becoming partner, or are you just scared Michael will be pissed?”

Keeping his voice as low and as steady as possible, Castiel said through his teeth, “Meg, Michael has nothing to do with this.”

“Right, and the big ol’ crush you’ve had on him for the past three years is nothing?”

Castiel did not answer, but his silence and his burning face were answers enough for Meg. She sat down in her chair, leaned back and put her feet on her desk, crossed at the ankles. “You are scared shitless that if he sees you as competition for the position of partner he will never see you as… more.” She crossed her arms over her chest, the personification of smugness. “Tell me I’m wrong.”

His tie was suddenly suffocating Castiel, and he had to loosen it before speaking. “Michael does not see me as competition. We are friends.”

“You are colleagues who sometimes go out after work with other colleagues,” Meg corrected him, and then she grabbed the magazine she’d been reading before Castiel came and leafed through it slowly. “You know what your problem is Clarence? Your problem is that you are stuck in the Friendzone.”

“The Friendzone?” Was this some sort of game? He could never tell when Meg was involved, but he was really not in the mood to play psychologist and patient.

“Yeah. You are good company for a couple of drinks along with the other boys and that’s it. Nothing more.”

“There’s no such thing as the Friendzone.”

“Not according to this.” Meg placed the magazine between them and then turned it upside down so Castiel could read the article. The title took up almost half of the right page in bright pink letters that looked like they were made out of bubblegum: _Nine Steps Out Of The Friendzone_.

“Is that Cosmopolitan?” Castiel asked as he skimmed the article.

“Cosmo is the holy grail of dating advice. You shall show respect,” Meg said, and her tone made it clear she was not joking.

“If it’s the holy grail of dating advice how come you are still single?”

“Clarence, I’m a free spirit. I’m single, but trust me, I get plenty of action.” Meg winked at him, and Castiel suddenly felt like this conversation was becoming a little TMI for him.

“Trust me, you follow these nine easy steps and Michael will be begging you to go out with him,” Meg said before quickly adding, “and then you are free to pursue that promotion.”

She clapped her hands, delighted, and Castiel rolled his eyes. “I told you I don’t care about-”

“Shhhh!” Meg lifted her perfectly manicured finger to silence him and then pushed the magazine towards him. “Do it for me, Clarence. Get the asshole of your dreams and get me that sweet parking spot.”

“No,” Castiel said, and believing their conversation over, he turned to go inside his office.

“Think about it and let me know,” Meg sang without looking at him.

***

The Roadhouse was only two blocks away from their office, and it was the bar most Shurley & Laufeyson employees frequented. Castiel had been there so many times he had lost count by now; he’d celebrated victories there, and he’d drank after lost cases. It was a place that was as familiar to him as his own office.

People crowded together around the wooden tables, laughing and sharing drinks, drowning out the music playing on the speakers. Gabriel still hadn’t arrived, but almost everyone from the firm and a few of his friends were already there and waiting for him, while a couple of waiters were rushed around the tables Chuck had booked, serving beers and pretzel bowls to the party. Castiel was sitting with Inias and Anna, but their discussion was lost on him. Michael was right across from him, in his tailored suit and carefully knotted dark red tie, laughing at something a girl Castiel vaguely recognized from accounting was saying to him. He looked perfect as always. Castiel took a large sip from his beer, forcing himself to tear his eyes away from Michael before someone caught him staring.

Thank God, Meg hadn’t come. She would have spent the entire night teasing him.

“Everyone, take your places,” Chuck said, raising his arms above his head to get their attention. “Kali just texted me. She and Gabriel will be here in a matter of minutes.”

Castiel stood right under the large ‘Happy Birthday Gabriel’ sign they had put up above their tables, squeezed between Inias and Chuck. A blonde waitress brought a birthday cake covered in so many candles they could barely look at it without going blind. It looked like a fire accident waiting to happen, but if it wasn’t extravagant then it was not Gabriel’s birthday party. The other patrons gave them amused looks as they all held their breaths with their eyes trained on the large double doors.

“Three, two, one...” Chuck counted down just as Gabriel pushed the door and held it open for his wife to come through first. “Now!”

“Happy birthday Gabriel!” they hollered all together, confetti falling like rain over them, and seriously, where had the party poppers come from? Castiel hadn’t seen anyone holding one.

Gabriel looked up with wide eyes and a beaming smile as his friends and colleagues cheered and yelled for him to get his ass over to his cake. He brought a hand over his heart and stared all around him, amazed. “You guys,” he said, “I had no idea. You didn’t have to.”

“Of course we did,” Chuck told him as the two embraced and patted each other on the back. “You had it highlighted with red on the email you sent me last month to remind me.”

Everyone sang at the top of their lungs, and even a few of the nearby tables joined in as Gabriel looked down at his cake, putting on his best fake surprised face. He blew out the candles, and Castiel clapped along with everyone else and teased him about telling them his wish, as tradition had it.

“You guys, my wish is the same every year,” Gabriel said, taking a candle out of the cake and licking the frosting from the end of it. “For us all to be able to celebrate together again next year.”

Anna gasped softly with tears in her eyes at the sentimental statement, but Castiel, who had already attended five identical surprise birthday parties for Gabriel, just waited for the punchline.

“Just kidding, I wished this cake was red velvet and guess what,” he held the candle he was about to lick clean next up so everyone could see the traces of red crumbs stuck to it, “it is!”

Yes, there was little difference between the scenario of each party, but that was one of the reasons Castiel enjoyed them as much as he did. He liked routine and rules, and he liked working in the same office with the same people every day. Castiel liked what was predictable and safe, even if his few friends teased him for it.

“Only the best for you, Gabe,” Kali told him as she leaned in for a quick peck. She pulled back and used a paper napkin to clean a few white traces of frosting from Gabriel’s mustache. It was a gesture so natural and yet so intimate that Castiel had to look away, smiling. No one would have guessed someone as reckless and fun loving as Gabriel would have hit it off with the judge who had thrown him out of her court every time she had seen him, but Gabriel had gotten that first date somehow, and their marriage a year ago had been attended by more than five hundred guests. Gabriel’s motto was go big or go home, after all. Castiel had to consider himself lucky to be in the inner circle of Gabriel’s friends. Not that he would ever use their personal relationship as an advantage for his career, but it was still nice having someone as open and friendly as Gabriel to brighten his day. Plus Kali was an excellent cook and very generous with her servings, so that was a bonus.

“Let’s get this party started!” Gabriel said in a loud voice, throwing his arm around Chuck’s shoulder and pulling him closer.

Now that everyone was mixing and mingling it was easy for Castiel to accidentally find himself standing right next to Michael. What a happy coincidence.

“Novak,” Michael greeted with a nod. “Didn’t know you were attending.”

Castiel didn’t point out how he had been one of the first to arrive. Michael might have been busy and not seen him. “Can’t miss Gabriel’s birthday.”

Michael hummed in agreement, his eyes following Gabriel as he walked among his friends and co-workers, poking fun at them. “He is something, isn’t he? Now if you’ll excuse me, I think I see Rachel with a few of her friends over there.”

And just like that he brushed past Castiel, face brightening up in the way it never did when he talked with Castiel. Another routine, but this time one Castiel surely did not enjoy. Actually, it was one thing that he thought would be better if it changed. If only he knew how.

Swallowing his disappointment down, Castiel turned his back to the celebration. He needed a drink as soon as possible to chase away the bitterness that was quickly rising at the back of his throat, and he needed to be alone for that. Or at least among strangers. With his shoulders slumping and as inconspicuously as possible, he sneaked away from his colleagues and collapsed on the first empty stool he found at the bar. Dropping his face, he stared at the wooden surface in front of him, unblinking until his eyes watered.

“You know there are only three reasons somebody drinks alone while his friends are having fun halfway across the room,” a cheery voice said from across the bar.

Castiel refused to take his eyes off of the water and beer stains left on the bar top in front of him. “Technically, I’m not drinking yet.”

“Good point,” the voice said again without losing any of its amusement. “What can I get you?”

“Rum and coke. Strong.” Lifting his eyes to look at the barman who had talked to him, Castiel forced himself to smile weakly. He was bitter but not an asshole.

“Coming right up.”

The man was tall, maybe taller than Castiel, with short, light brown hair and wide shoulders. He grinned at Castiel before reaching under the bar to find a glass to prepare his drink. His movements were precise and efficient as he added the ice and poured the dark liquid with practiced ease. He was good-looking, Castiel observed. More pretty than handsome, but definitely good-looking enough to leave a pile of broken hearts in his wake. Speaking of broken hearts, Castiel was reminded of why exactly he was drinking, and his mood soured again.

“So, why are you drinking alone?” the barman asked as he slid the glass towards Castiel.

Taking a large sip from his drink, Castiel closed his eyes and felt the burn traveling down his throat and warming up his body. “You said there are only three reasons. Take a guess, and I’ll tell you if you are right or wrong.”

“Oh, a game. I like games.” The man crossed his arms over his chest, leaning with his hip against the edge of the bar. “Let’s see. One, you actually like nobody from your group but you don’t have anyone else to hang with. Two, you are a miserable asshole and nobody likes _you,_ but everyone else got invited so they had to invite you, too. Three,” he lifted an eyebrow and grinned, “it’s a case of broken heart.”

“Well you are right, it’s one of those three reasons,” Castiel answered, fixing his eyes on the barman, using his best poker face. “Can you guess which one?”

The barman’s mouth lifted at one corner, his head tilting to the side at just the right angle to catch the light and distract Castiel with how warm and green his eyes were as he studied Castiel, trying to figure him out. “You are an interesting guy.”

“It’s Castiel.”

“Castiel, huh? That’s an unusual name. It suits you. I’m Dean, by the way,” the barman - Dean - said. Then he frowned. “You’re miserable, but you don’t look like an asshole,” he finally declared and bent forward, elbows resting on the bar, until his eyes were at the same level with Castiel’s. “I’m choosing curtain number three.”

“We have a winner,” Castiel said, and despite all odds, he felt the beginning of a smile tugging at his lips. He threw back his drink.

“So who are they?”

“Black hair, freshly shaven, dark gray suit and red tie,” Castiel whispered conspiratorially without even having to look behind him to remember what Michael was wearing. He had spent half the night pretending not to stare, after all.

Dean’s eyes left his for a second to look at where all Castiel’s colleagues were celebrating, and then they returned. “He’s handsome, I’ll give him that. Care to share the full story?”

Downing the rest of his drink in one go, Castiel pushed the glass towards Dean. “Get me another one, and maybe I will.”

A second glass was placed in front of him. Castiel tipped it towards Dean in a small toast. One beer and two glasses of rum and coke were usually not enough for him to start talking, but they were a good start, and Dean seemed like a good listener. Well, why the hell not. “He is-”

“Leaving,” Dean interrupted, pointing with his eyes towards the door and then wincing, “with his arm around a girl. Ouch.”

Did Castiel want to know? The logical answer was no, it would do him no good to turn around and see who she was, and if it really was Michael, but Castiel needed to see for himself for some sadistic, self-destroying reason. So he turned. He caught sight of them just as the door closed behind Michael and the girl from accounting he had been talking with earlier.

Suddenly, the only thing Castiel could feel was the loud ringing in his ears. The noise and the music all around him faded as he focused his eyes on the closed door, waiting to see if it would open again. Maybe Michael had just helped her find a cab or something. Maybe they hadn’t really left together. Maybe…

“I’m sorry, Cas. Are you okay?”

Dean’s voice made its way through the fog clouding Castiel’s mind and brought him back to reality. Michael had left. With her. And he had not returned.

The stool screeched as Castiel turned around again and sagged against the bar top.

“Fine.”

The image of Michael with that woman was seared behind his eyelids, and he couldn’t make it go away. He needed something stronger.

“Get me a shot. Whiskey,” Castiel asked Dean. “And pour one for yourself too.”

Dean prepared the shots without comment, but no matter how subtle he was, he couldn’t hide the pity with which he looked at Castiel. They downed the shots, and then Castiel asked for a second round.

Round three was where Dean drew the line. “That’s enough, Cas. I’m cutting you off.”

“I’m not drunk,” Castiel complained even though his limbs felt looser already and uncoordinated. He was not drunk yet, but he was definitely buzzed, and stopping was probably the right choice. Not the choice he felt like making at the moment, though. “Get me another shot.”

“I’ll call you a taxi, and then I’m sending you home. Drink this.” Dean placed a glass full of water in front of Castiel. Although he really wanted to just throw it across the room, Castiel knew that Michael leaving with someone else was not Dean’s fault. It wouldn’t be fair to act like a brat to someone who was just trying to be nice. He drank the water obediently.

Dean shook his head, sighing. “You know, a guy like that is probably not even worth the trouble. I’m sure someone like you can easily find someone better. I bet you have a ton of secret admirers.”

Castiel didn’t want anyone else, but he didn’t have the strength left to say it. Meg’s voice emerged through his memory to remind him of his problem. _You are stuck in the friendzone, Clarence._

And just like that Castiel’s brain came to a record-scratch moment. He was stuck in the friendzone. He was stuck in the friendzone.

“I have to get out,” he said.

“Wait till I call you a taxi first, okay?” Dean said with a finger raised in front of him to keep Castiel still.

“No. That’s not what I mean.”

“What?”

“I have to make Michael fall for me.” It was obvious. Meg was right all along, damn her. He had to stop hiding. Except… “Except I don’t know how to do that.”

Dean blinked. “Well, if you need any help,” he said slowly after a beat.

Castiel lifted his eyes to stare right at him and then pushed himself up so fast he went a little dizzy. “You’d do that?”

Dean dropped his eyes, scratching the back of his neck as he said, “Sure. I mean we could go for coffee or something and talk about it, you know? Doesn’t have to be-”

“Saturday? Are you free?” Castiel reached and grabbed him by the elbow. “Please.”

Dean froze in place with his mouth hanging open and then cleared his throat. “Sure thing. Saturday. It’s a date.”


	2. Step 2: Look your best

  
A small bell jingled as the door opened and closed. The scent of freshly ground coffee and burnt sugar enveloped Castiel the moment he stepped his foot inside the coffee shop and chased away the chill of autumn’s last days. It was early for a Saturday morning, but almost all the tables were already occupied, and a dozen people were waiting in the queue to order their coffee and breakfast. No one looked like they minded waiting. They were all content to chat with their friends, or in the case of a young girl and a dark haired boy, hold hands and steal kisses. The coffee must have been excellent if there was such a crowd already.

Briefcase in hand, Castiel wondered whether it would be better to find a table and wait for Dean or line up with everyone else, when the crowd parted a little, and through the open space he saw Dean with his face pressed against the food display case. Castiel had been so excited for today that he had arrived ten minutes earlier than what they had agreed, but Dean had apparently arrived even earlier than that. Castiel was impressed with his punctuality.

Castiel pushed his way through all the people until he was standing right next to him, but Dean was too busy frowning down at all the croissants, tarts, cakes and pies the store had to offer to notice him. He wasn’t drooling, but he was close.

“Hello, Dean.”

Dean jerked around with wide eyes and then, flushing all the way up to his hair roots, he grinned. “Good morning, Cas. Sorry, I was supposed to be keeping an eye out for you, but they have five different kinds of pies and I really, really can’t choose which one I want.”

Castiel surveyed the pies Dean had been looking at. They really did look delicious. He could understand why Dean couldn’t decide.

“What’s your favourite flavour?” Castiel asked, taking a step closer to read the handwritten cards in front of each pie.

“All of them.”

“How are you going to decide then?”

Dean shrugged, tracing circles with his finger against the glass. “What’s _your_ favourite flavour?”

“I don’t have a favourite flavour.”

Dean turned to him, horror written all over his face, like Castiel had just admitted to the worst crime possible.

“I don’t eat pie that often,” Castiel said quickly, hoping this explanation was good enough.

“Dude, you're getting the pie.” Dean sounded so serious that Castiel didn’t dare tell him he had already had breakfast before coming here. He just followed him to the back of the line.

“I wanted to get everything before you arrived, so only one of us would have to stand in line,” Dean said six minutes later, placing their tray on the only empty table. They had been lucky. A very tired-looking student had decided that this place was too noisy and crowded for him and had gathered his things to leave just as they had turned to search for a place to sit. “It didn’t occur to me that I didn’t know how you drink your coffee until I got here.”

Castiel draped his trench coat over the back of his chair before sitting down and reaching over for his cup and plate. His caramel macchiato smelled delicious and felt hot against his palms where they touched the cup. He pulled it closer to him to blow the steam away and then smiled at Dean. “Well now you know.”

“I know that you don’t like coffee.” Dean left his own cup to the side and immediately brought the plate of apple pie – _gotta_ _go for the classics, Cas! Plus apples are in season –_ in front of him. “Why even get coffee if you drink it with so much crap inside that it doesn’t even taste like coffee? I mean, okay, I can give you sugar and maaaaybe I can back off on the cream thing but caramel, too?”

“It keeps me awake and tastes like cookies,” Castiel said, hiding his smile behind his cup. Dean had been horrified when Castiel had ordered his drink. To him the only acceptable _real_ coffee was black and bitter. To appease him, Castiel had ordered a piece of pecan pie, even though he already knew he wasn’t going to eat it. He was still too full from the omelete he’d had for breakfast. Although he suspected Dean wouldn’t say no to a second piece after he was finished with his own.

Dean took a bite of his pie and closed his eyes as he chewed and swallowed. Evidently the pie tasted as good as it looked, if the pure bliss written all over his face was anything to go by.

“Cas, I think I just met God.”

“Is it the best pie you’ve ever had?”

“No, but every pie brings me a step closer to nirvana,” Dean said with beaming eyes.

He grinned at Castiel and then quickly looked down at his plate again. His cheeks were flushed, making the freckles Castiel hadn’t noticed last night almost fade against his skin. Maybe the flannel he was wearing above his tee was warmer than it looked.

“So what’s the plan,” Dean said, cutting another piece from his pie.

“This is the plan.” Castiel opened his briefcase and took out Cosmopolitan, easily finding the article Meg had shown him a few days ago. He had had to steal it from her desk while she wasn’t looking and pray really, really, _really_ hard she didn’t notice.

“Nine steps out of the friendzone?” Dean asked, reading the title and then pointing his fork at Castiel. “That’s your plan? Cas, you do realise there is no such thing as the friendzone right? There are only people who don’t have the guts to ask the other on a date.”

Castiel left the magazine open on the table between them. “It’s a little more complicated than that. Haven’t you ever met someone that you really wanted to be something more, but they never thought of you like that?”

Dean narrowed his eyes at the magazine, staying silent for almost a minute. Castiel was worried he had offended him somehow, but then Dean sighed, shoulders sagging.

“Yeah, I’ve met someone like that. Someone I could only admire from afar without ever hoping they would notice I exist,” he admitted in a low voice and a soft smile, looking at Castiel through the thick of his eyelashes and then quickly looking away.

“So you do understand. Dean, will you help me?” Castiel had to tip his head lower to catch his eyes again. “Please.”

Uncertainty flashed across Dean’s eyes, along with something else that Castiel couldn’t identify. Dean took a deep breath and then shook his head, a small laugh escaping his lips. “You know what Cas? I will. Why the hell not? What’s the first step?”

***

“I don’t understand, why do I need new clothes?” Castiel asked as a tailor took his measurements in front of a floor-to-ceiling mirror.

“Because Cosmo-advice number two is to always look your best, and no offense Cas, but your clothes don’t look like they fit,” Dean answered from the couch he was lounging on, going through the magazine for an interesting article to read. “Oh look, Cosmo-sex tips!”

“My clothes are comfortable,” Castiel complained, looking at Dean over his shoulder and making the tailor pinch him by accident with a pin – _please don’t move around._

“Comfortable is not sexy. Even if you do come dangerously close,” Dean muttered, making a disgusted face at whatever sex tips he was reading. “That’s why we are getting you new ones. There’s nothing sexier on a man than a perfectly tailored suit.”

Castiel frowned at his reflection. The suit he was trying on was nice but nothing spectacular, and he really didn’t see the need for new clothes. Although, taking a step back and thinking about this more thoroughly, Michael was always impeccably dressed. So maybe there was something to this Cosmo-step.

“It’s true sir, tailoring makes all the difference in how clothes look on you,” the tailor said through the pins between his teeth. “Once I am done with the suits you and your boyfriend chose, you’ll look good enough to walk down a red carpet.”

“Oh he’s not... we’re not-” Dean stammered, a flush creeping across his cheeks.

How warm was that flannel shirt anyway? “We are just friends,” Castiel said.

“I’m sorry. I didn’t mean to presume,” the tailor apologised and kept on doing his work in silence.

“I. Uh. I’m going to look for ties,” Dean said clearing his throat. “Two should be fine for a start right?”

“Yes, thank you, Dean.”

Three new suits, two new ties and an appointment to bring in two of his old suits for tailoring later, Castiel and Dean left the shop. Castiel thought their trip was a success. Everything they bought was in colors he liked, and if the fit was a little tighter than what he was used to then he would get used to it. He felt refreshed and full of energy. Maybe a little change was exactly what he needed after all.

“Do you think I need a haircut?” he asked Dean, squinting against the sun blinding him after so long inside the store. He caught his reflection in one of the storefronts they passed by and stopped to scrutinize his appearance, only for Dean to drag him back to his side.

Dean shrugged, giving Castiel a once-over. “I kinda like your hair. Makes you look like you didn’t try. Effortlessly cool.”

“It makes me look like I just woke up.”

Dean reached over and threw an arm over Castiel’s shoulders, guiding him down the road. “Yeah, wake up is not the verb I was gonna use. It looks sexy though, so don’t change it.”

“You think my hair is sexy?” Castiel had to admit he was flattered. Usually people had less kind comments about his hair.

Dean released him and ducked his head, playing with the end of his jacket’s zipper before zipping it up to his chest. “Well, it’s the truth.”

“Dean Winchester, you did not cancel on me so you could go out on a date.”

The voice made Dean jump and turn guiltily towards a red-haired woman, who was crossing the street towards them, her eyes narrowed at him and threat in her every stride. “What the hell, Dean. You could have at least told me,” she said punching him in the arm twice with enough force to make him wince and pull back to get away.

“Relax, Charlie. It’s not a date. Cas is just a friend who needed help.”

Charlie paused and stared at Castiel, wheels turning inside her head before something clicked. “Cas? Oh you’re the lawyer guy from the bar,” she exclaimed and without a warning she wrapped Castiel in a bone crushing hug. “I’m Charlie, it’s very nice to meet you.”

“Nice to meet you, too?” Who was that woman and why was she hugging Castiel? No matter how much he wracked his brain, he couldn’t remember seeing her before. He turned to look at Dean over Charlie’s head in confusion, and he shrugged in apology.

“I’ve heard so much about-” she started all bubbly and smiling, but then, noticing the weird face Dean was making at her, she closed her mouth. He looked kind of funny actually, something between having a stroke and realizing he forgot to lock his door. Although Castiel sincerely hoped neither of those two were true. Charlie released him and took a step back.

“Cas, this is my friend Charlie,” Dean said through gritted teeth. “Charlie, I’m sorry for canceling on you, but Castiel was in dire need of a wardrobe change.”

“You guys are shopping?” Charlie seemed to perk up at that. “Why didn’t you tell me to come? I could have helped.”

“You have terrible taste.”

“I do not,” she protested. “Lesbians are fashion icons, you know.”

Dean rolled his eyes. “Not all lesbians, and especially not the queen of nerds. Remember that time I had to convince you not to go to that job interview wearing a red business suit?” he accused her, crossing his arms over his chest.

“That red suit was fabulous,” she shot back. “And it’s the Queen of Moondoor to you, Handmaiden.”

“Not until tomorrow, kiddo! Now get lost.”

Charlie narrowed her eyes and pointed finger guns at Dean as she walked away backwards. “Remember this when you come to my service tomorrow. I’ll have you on latrine duty.”

“There’s no latrine duty!” Dean frowned at her walking away with his hands on his hips.

“Bye, Cas! It was nice meeting you.” With a last wave at their direction and a wink that made Dean blush lightly, she disappeared among the crowd.

Dean rubbed the back of his neck as they stood side by side, watching the people go by. “Sorry about that. Charlie can be too enthusiastic sometimes,” Dean said after a beat.

“I think she is lovely.” Charlie looked like a bundle of endless energy and positivity. Castiel liked her. “You talked to her about me?”

Dean’s eyes widened to double their size, and he quickly looked away. “I- You know- Our meeting was kind of… interesting.”

“I guess that’s true,” Castiel said and then after a pause, “-Handmaiden.”

“Oh man,” Dean groaned.

“Care to explain?” Castiel had to admit Dean was cute when he got embarrassed. It was a refreshing change to his usual confidence and constant flirting.

“It’s just this LARP event we go to- wait, do you know what LARPing is?”

“I have no idea?” Castiel admitted.

“Well it’s a kind of role playing game, where we dress up and act as medieval and fantasy characters.” Dean must have noticed the small smile on Castiel’s face because he quickly added, “It’s not as lame as it sounds, I promise.”

Castiel bit his lower lip, trying to keep his smile from growing. “And you are a handmaiden?”

“I’m a warrior. You’ll see, I look really cool when I’m wearing my costume.” He lifted his chin defiantly, but there was a hint of playfulness to the curve of his mouth. “I’ll send you a picture tomorrow.”

“You have my number.”

***

When Castiel received the picture while cooking his dinner on Sunday, he thought Dean really did look cool. Handsome too. Like the prince all girls dream will come and sweep them away on his white horse. He was posed in all leather, with chainmail around his neck. It was kind of sexy in a weird, medieval kind of way. Without thinking much about it, Castiel saved the picture and replied with a heart eyes emoji.

***

Castiel adjusted his new tie nervously, inspecting his appearance in the elevator mirror one last time before the doors opened and he had to face all of Shurley & Laufeyson. Dean and the tailor had been right. The suit fit him like a glove and hugged every part of his body perfectly, showing off his best assets. It was like this was a completely different suit to the one he had tried on.

He took a deep breath and stepped outside the elevator without his trench coat for the first time in six years. Hannah, Gabriel’s assistant, who was in the reception room, did a double take when she saw him, her mouth hanging a little as he walked past her. That was a good sign. Castiel felt his confidence go up a notch. He did look good, didn’t he?

Not to brag, but Castiel counted at least half a dozen heads that turned to watch him in wonder as he walked towards his office. For the first time since Meg started working for him, she was at a loss for words.

“Castiel-“ Her mouth opened and closed a couple of times, her eyes bulging out of their sockets.

“What happened to Clarence?” Castiel asked just to annoy her. That seemed to sober her up.

“What’s with the extreme makeover lawyer edition?”

“You don’t like my new suit?” Castiel opened his arms, doing a little circle in front of her.

“You know you look delicious, Clarence.” Meg leaned back in her chair with a thoughtful expression. “Is this about the little talk we had a week ago?”

“Our talk?” Castiel walked into his office, knowing full well Meg was going to follow him and corner him in there to interrogate him. Which she did.

“The friendzone talk.” She made herself comfortable, sitting on the edge of his desk while Castiel took papers out of his briefcase.

“Friendzone? He calls me Novak, Meg. We are not friends.” Hopefully making her realise how ridiculous she sounded would keep her from finding out how close to the truth she was. “He doesn’t even care that I exist.”

“That’s not how our conversation went.” Meg raised an eyebrow at him expectantly. She was not going to drop this subject easily.

“What do you want me to say? Maybe I just needed a change.” Castiel kept his face toward his desk, turning on his laptop and re-arranging everything in clean piles.

Meg tilted her head to the side, waiting for him to say something more, but Castiel kept his mouth shut stubbornly. Finally, with an exasperated sigh, she got up and left with a final, “Just be careful, Clarence.”

All in all, Castiel had to admit the new clothes were a success with everyone but Michael. Castiel spent the whole day finding excuses to wander out of his office where Michael might be. He went to the bathroom six times and to the kitchen another four, but the two times Michael passed by him he didn’t react other than with a quick nod and a ‘Novak’ as acknowledgement. Everyone else complimented him. Gabriel cooed for ten minutes how handsome Castiel looked, and even Chuck lifted his eyes from his cat tumblr to see what all the fuss was about. The only time Michael commented on Castiel’s appearance was when they shared the elevator on their way out, and Michael, looking a little confused, asked, “Where’s your trench coat.”

“At the drycleaners,” Castiel answered smoothly, a line he had been practicing all weekend in front of his mirror. Did he nail the smooth, nonchalant vibe he was going for? Hell, yeah! Did Michael appreciate it? Definitely no.

“Maybe it’s time to get a new coat,” Michael said, looking straight ahead. “That one is kind of old, isn’t it?”

And that was that. The elevator doors opened, and Michael walked out without a second glance.

It was stupid, but Castiel was disappointed. It was not like he expected some new clothes would be the magic solution, but still, he expected some kind of reaction. Fucking Alfie, the mail boy, had complimented him today.

Without even noticing, Castiel walked past his car and down the road until he stopped in front of a familiar building.

Dean was behind the bar, a sight that shouldn’t have been as heart-warming and as comforting as it was, but Castiel was tired and kind of miserable. Dean looked like the sun among rain clouds, and Castiel was drawn to him like a moth to light.

Dean spotted him as Castiel walked towards the bar, and his mouth dropped open. He quickly excused himself to the customer he was talking to and gestured for Castiel to follow him to a part of the bar that was less crowded.

“Dude, you look-“ Instead of finishing his sentence Dean waved in a vague circle at all of Castiel. Judging from the wonder in his eyes, Castiel decided this was a compliment. He did not feel like he deserved any compliments at the moment, though. He felt more like a dog that got caught in the rain.

“Miserable?”

“I was gonna say hot as hell, but we can go with yours, too. Rough day?”

Castiel supported his head on his hand, all energy drained out of him. “You can say that.”

“Want a beer? On the house.” Castiel had a beer menu in his hand before he could protest. “Wanna talk about it?”

“I guess I’m just disappointed,” Castiel started and quickly recounted the whole day, with emphasis on how _not_ interested Michael had been.

Dean threw his cloth on the counter with a curse under his breath. “What a dick. Honestly, Cas, you can do so much better. What do you even see in him?”

“He is successful, handsome, charismatic.” Castiel raised a finger as he counted down.

“I didn’t know you cared about all that stuff,” Dean said in a cold voice. “Didn’t think you were _that_ kind of person.”

Castiel rubbed his palm over his face, trying to gather his thoughts. “I don’t. I’m not.”

Dean stared at him hard, jaw set like he was weighing something in his mind. Castiel could only hope the decision would be favourable to him.

After half a minute, Dean’s face relaxed. “For what it’s worth, I liked your trench coat. It was like your signature. Your bat suit.”

“Bat suit?”

“Yeah, because Batman has his iconic costume, and you…” Dean trailed, realising nothing he was saying rang a bell in Castiel’s mind. “You don’t know Batman?”

“I know Batman,” Castiel said defensively. “I’m just not very familiar with all the details.” Then, because Dean still looked at him like he had grown a second head, he decided to change the subject. “You’ve seen me a handful of times and you’ve already decided the trench coat is my signature?”

Dean scratched the edge of the counter nervously with his nail. “I wouldn’t call it a handful of times. I’ve seen you around.”

“Around?”

“I’ve worked here for at least five years, and you and your colleagues are regulars.” Dean shrugged, avoiding to look Castiel in the eye. “Like I said, I’ve seen you around.”

Castiel couldn’t remember seeing Dean before they met that night he told him about Michael. Of course Castiel never used to sit at the bar or interact with the bartenders directly. Some of the waitresses, like a short blonde one that worked at the Roadhouse as long as Castiel had frequented, he knew and recognized, but not the bartenders. Dean on the other hand, not only knew him all these years, but remembered the trench coat as well. He liked it too.

“I’m sorry we didn’t meet earlier then.” Castiel meant it. It didn’t matter how he and Dean met, or why they started talking, Castiel liked Dean, and hopefully he could get a good friend out of this crazy situation.

Dean grabbed a plastic bottle of water he kept under the counter and lifted it towards Castiel. “I’m sorry your secret crush is a piece of shit.”

“I’ll drink to that.” Beer glass and plastic bottle bumped without any noise, but the sentiment was there.

“So what about our plan?” Dean asked, drinking a big gulp of water, a drop escaping the corner of his lips and making its way down his jaw and neck until it disappeared inside the collar of his shirt.

Castiel looked away. “What’s the next step?”


	3. Step 3: Don’t be readily available

  
_> >Dean W. 09:35_

_Hope you’re feeling better today :)_

Castiel smiled down at the simple message. Such a simple gesture, and yet it made Castiel’s heart swell with fondness. Dean was a very kind and caring person, and Castiel was lucky they were friends now. And he really was feeling better today. He had been feeling better since last night when he met Dean again actually, but he still appreciated how Dean wanted to check up on him.

There was a quick and distinctive _taptaptap_ against his office door frame, and Meg walked in without waiting for an answer. “I got those files you asked for,” she said, bringing a couple of folders to his desk but pausing and narrowing her eyes at him before she reached it. “What’s with your face?”

“What’s wrong with it?” Castiel touched his cheek and then his jaw. His stubble scratched his fingers, he needed to shave when he got home that night. “Do I have something?”

“A stupid smile. What’s going on, Clarence?” Meg lifted a perfect eyebrow at him in question, but her smile showed she had her suspicions.

He ducked his head, trying to hide the burn rising up his cheeks and pretended to focus on the paper in front of him. “I have no idea what you are talking about.”

"Of course you don’t.” Meg’s grin doubled in size as she slowly and theatrically left the folders on the desk. “I’m sure that text you got a minute ago has nothing to do with it.”

“I didn't- I am-“ Castiel stammered out, feeling the burn travel further and reach his ears. How did she even know about the text? She was in the other room. “Don’t you have any work to do?”

“You're right. I have to paint my nails. Don’t bother me for the next couple of hours while my polish is drying.” She walked away, confidence in her every step.

“Remind me again, why do I keep paying you?” Castiel asked her retreating back.

“Because I’m better and faster than all the assistants you’ve ever had combined,” Meg answered with a hair flip and a wink over her shoulder.

Castiel couldn’t argue with that.

From his desk, the folders Meg had brought and his phone stared at him, one reminding him to get back to work, and the other calling to him, like a little horned devil whispering in his left ear. The correct choice would be to get back to work. He was not getting paid to play with his phone, but...

Just a quick text. Dean was so nice, and Castiel didn’t want to be rude.

He grabbed the phone and opened the messaging app, typing away a quick reply. His thumb hovered above the screen, wondering which emoji would be more appropriate to use, when another knock, followed by Gabriel announcing his presence with a very loud ‘morning Cassie!’ sent his phone flying out of his hands in surprise.

“Relax, it’s just me,” Gabriel laughed. “Are you okay?”

Castiel eyed his phone on the floor - screen facing down unfortunately – and got up to greet him. “Yeah, sorry about that. You caught me by surprise.”

“Caught you daydreaming, Novak?” Michael asked from the door, because of course the one time Michael found his way to Castiel’s office was when Castiel made a fool of himself. Yeah, good job, Novak.

“No. Just... just,” he said lamely for the second time that day (damn what was wrong with him) and because he had no idea how to continue that sentence, he closed his mouth and waited for someone to fill the awkward silence.

The vote fell on Gabriel. “Michael, we’ve talked about this. No last names. We are a big family here.” He clapped Castiel on the shoulder and then pointed a finger at him. “Tonight. Guys and beers. You, me, Michael, Inias and Ishim. Are you in, bro?”

Drinks with the guys? Yes, Castiel was totally in. That was a great opportunity to spend some time with Michael. Yes, it was the perfect opportunity.

Except it wasn’t.

What was rule number three again? Don’t be readily available at all times. But he was available at the current moment. He was not ditching anyone else. It was Tuesday, what else would he be doing that night? On the other hand, what did it say about him that he didn’t have any other plans? Maybe Michael would think he was a loser. What would he be doing instead of going out with them?

“Cassie.” Gabriel snapped his fingers in front of Castiel’s eyes. “Are you still with us?”

Rule number three.

The words escaped his lips before Castiel could stop them. “I have a date.”

“I’m sorry, I didn’t catch that.”

Castiel stared straight at Gabriel and repeated, louder this time, “I have a date. I’m sorry, I can’t make it tonight.”

Gabriel and Michael both stared at him with wide eyes and then:

"You have a date?” Michael asked, doing a very bad job at hiding his surprise. It was not a bad look on him. Far better than indifference anyway.

Castiel straightened his back, lifting his jaw. “Yes, I do.”

“Do I know them?” Gabriel asked, leaning closer and lowering his voice. “Is it someone from the firm? Because we do discourage it, but I will look the other way for you.”

More likely he’d look the other way so he would always have the inside scoop on the firm’s gossip. Gabriel was consistent like that.

“No, no. He is not from the company,” Castiel said quickly. He had to keep the details vague, if he wanted to be believed. “It’s still pretty new actually. I don’t want to say anything and jinx it.”

“Of course, we totally understand. We won’t say a thing to a soul,” Gabriel promised immediately, raising his eyebrows at Michael in warning.

It was a whole, very awkward, five seconds where Michael just stared at Castiel with wide eyes. It was only after Gabriel cleared his throat and elbowed him in the side that he blinked back to focus.

“Secret’s safe with us...” he said, his sentence rising at the end similar to a question.

With a quick salute, Gabriel took his exit, Michael following closely behind him, but not before turning to look at Castiel with… something in his eyes. Wonder? Perhaps new found interest, but that might have been just Castiel projecting. But there was definitely something there.

Castiel waited until he was sure they wouldn’t come back. Then, heart still fluttering like a scared bird, he ducked under his desk in search of his phone.

“Please be okay, please be okay, please be okay.”

The phone was still lying screen down on the floor. He reached for it and after only a moment of hesitation picked it up and turned it around to see that the screen was completely shattered. His last shrivel of hope died when he tried to open it and all he got was the black screen of death.

Wonderful. Now he was without a phone, and he couldn’t answer Dean’s text. Oh God, and he had just lied to both Michael and Gabriel. Could this day get any worse?

 

***

  
The Roadhouse was as busy as always when Castiel got there after work. Originally, his plan had been to go back home and order Chinese, but the idea of Dean wondering why Castiel never answered still bothered him, so he decided to stop by and apologise first. It was the polite thing to do, after all.

He could see Dean behind the bar from afar, talking to a couple of girls who were blushing and twirling their hair around their finger as he gave them his most charming smile. The girls laughed at something Dean said as Castiel made his way towards them, but he only caught the last part of their conversation.

“- saying the truth,” Dean said, winking at the dark-haired girl before he caught sight of Castiel. “Well, look who’s here. Sorry ladies, I’ll be right back.”

Dean waved Castiel over to the other side of the bar where there was an empty spot, while the girls pouted and begged him not to be too long.

“I see you have a fan club,” Castiel said, trying to ignore the sudden burning in his stomach. Weird, all he had had for lunch was a salad.

Dean gazed back at the two women and then bit down a smile. “Every good bartender does. They are the best tippers.” He poured a glass of beer from the tap – dark, with no foam, just like Castiel liked it – before placing it in front of Castiel. “It’s our little secret though,” he added with a wink.

Castiel took a sip of his beer, letting the alcohol relax him. “Your secret's safe with me.”

“Missed me already?” Dean joked using a cloth to wipe the counter between them.

“Maybe I did,” Castiel said, gazing at Dean until the other man had to avert his eyes, fingers playing nervously with the cloth he was holding. “Or maybe I wanted to apologise for not answering your text this morning. My phone had an unexpected malfunction.”

“Don’t worry about it. I figured you had more important, lawyer-y stuff to do.”

Dean was looking everywhere but at Castiel, who had to reach over and place two fingers on Dean’s wrist to get his attention. “I tried to answer the moment I got the text, but I dropped my phone and broke it.”

The beginnings of a smile appeared on Dean’s face. “That sounds very graceful.”

“It wasn’t.” Castiel shrugged, wrapping his hands around his beer. “Meg is getting me a new one tomorrow morning. Until then, I basically live in the stone age.”

“So, what’s the news from the front?”

“The front?”

“Our code friendzone operation? Or would you rather call it Cosmo-plan? I like Cosmo-plan, it has a nice ring to it.”

That’s right. Castiel had completely forgotten about that while he and Dean were talking. He hadn’t told Dean what had happened today.

“I think it’s going good,” Castiel started, planning to explain first what step three was, and how he was proud of himself for actually sticking with it even though he really wanted to go with Michael and the others. “I was in my office today- is something wrong?”

Dean was staring at him with wide eyes, his head tilted to the side with a weird smile, like he was trying really hard to communicate something to Castiel without actually speaking. The message was lost on Castiel though.

“Dean, I don’t-“

“Cassie!” a very familiar voice exclaimed from behind Castiel’s back. “I thought you had a date tonight. Don’t tell me you ditched us to drink alone.”

Gabriel slid an arm around Castiel’s shoulderm, while Dean pretended to clean some glasses. From the corner of his eye, Castiel could see Michael, Inias, and Ishim approaching them as well. He was such an idiot. Of course they would come to the Roadhouse. When they said drinks they always meant here. Fuck. He needed an excuse for being here alone and fast.

He peered at Dean who shook his head helplessly at Castiel. “You see, I had a date but then...”

“Did you get stood up, Novak?” Michael asked, coming to stand on the other side of him.

Castiel didn’t know what was worse, telling them that his date had never shown, or admitting that the date had been a lie from the very beginning? Either way he'd look like a fool.

“It’s my fault,” Dean jumped in their conversation unexpectedly. Gabriel and Michael both turned to him startled. “I was supposed to take him on a date tonight,” Dean explained, signaling at Castiel to just go with it, “but I had to cover for a friend last minute. Castiel is wonderful enough to keep me company until my shift ends.”

Castiel had no idea how Dean had caught up to his lie so quickly, but he was immensely thankful for being saved. At that moment, Dean could have asked for anything, and Castiel would have given it to him.

“He has a date... with you?” Michael eyed Dean from head to toe, one eyebrow raised.

“Sure thing, sir,” Dean said, straightening his back and puffing his chest out, giving Michael the most charming smile Castiel had ever seen on him. “We are going for dinner after I finish.”

Gabriel laughed, squeezing Castiel and then releasing him, while Michael touched his tie in a gesture Castiel knew he did when he felt he was losing at court. He couldn’t blame him, Dean was very handsome and could be downright irresistible when he tried. His fan club at the other side of the bar could testify to that.

“Well, we’ll leave you two lovebirds alone then,” Gabriel said and led the others to a table at the other side of the room.

When he was sure they were out of earshot, Castiel dropped his face in his hands, groaning.

Dean placed another glass of beer in front of Castiel and patted him on the shoulder comfortingly. “That was close. Good thing I think faster than you. Wanna tell me why they think you had a date tonight?”

Taking a large sip of the new beer, Castiel quickly told Dean about what had happened that morning and explained why he hadn’t gone out with them.

“I was so stupid. Why did I have to say a date? Now I’ll never have a chance with him.”

Dean leaned on the counter and tilted his head to catch Castiel’s eyes, offering him a smile. “Trust me Cas, there is no faster way to get a guy’s attention than making yourself unavailable. Plus, you got yourself a date with a hot piece of ass like me? I don’t think Michael can do better than that.”

Castiel rubbed his thumb on the glass, wiping away the condensation at the bottom. Despite Dean’s efforts, he was still feeling terrible.

“And now he knows you are into guys,” Dean tried, reaching over to place his hand on Castiel’s arm and rubbing comforting circles with his thumb.

Castiel deflated like a leaking balloon, pressing his fingers against his eyelids until he saw stars. “I’m gay. I’ve only ever dated guys, he knows that.”

“Seriously?” Dean asked surprised. “You’ve never done anything with a woman? Not even in high school?”

“Well there was Daphne Allen when I was fourteen, but that ended pretty quickly once I figured I was going to the football games to watch the players and not the cheerleaders.” High school had been a pretty confusing experience for him to say the least. “Oh and Meg.”

“Meg, your assistant you stole Cosmopolitan from, Meg?” Dean’s eyebrows had almost reached his hairline.

Castiel shrugged. “It was new year’s and we were both drunk. We made out after the countdown for a hot minute, and then she threw up all over my shoes.”

Dean barked out a laugh. “Sounds like fun.”

“It was, actually.”

From a few meters away, the girls Dean had been talking to when Castiel had come raised their arms to get his attention. Dean acknowledged them with a nod and a smile. “Duty calls,” he said. “Beer’s on me tonight.”

Before Castiel had time to thank him properly, Dean sauntered away, shoulders pulled back and flirty glint in the eye. The girls were already swooning after him. The brunette leaned forward and touched him on the arm, letting her fingers linger on Dean’s bicep before she pulled away and tossed her hair back, exposing her long neck.

Castiel looked away, his stomach a tight knot.

Even though it was a Tuesday, the Roadhouse was as busy as ever, and Dean couldn’t make much time to chat with Castiel, except for the couple of times he refilled his glass. The third time Castiel had stopped him and asked to switch to something non-alcoholic, and Dean had quickly produced a virgin mojito that tasted better than Castiel had expected. The little orange umbrella was a bonus.

Customers came and left, and even the two women were putting on their coats to call it a night, but not before the dark haired one had slipped a napkin with her number towards Dean. When Castiel saw Dean throw it away in the trash discreetly as soon as she had turned her back, muscles he hadn’t realised had been tight immediately relaxed.

That was weird. Castiel was not jealous of Dean, he had no reason to be. They were just friends. And yet his heart felt infinitely lighter when Dean approached him again, the girl’s number already forgotten.

“Your friends are getting ready to leave. You’ll be free in a few minutes,” Dean said, and Castiel turned around to see that they really were getting up from their table. Gabriel waved at him with a wink that was not subtle at all, while Michael gazed at them, frowning.

“I had a better idea, actually.” Castiel had spent the last few hours thinking about this. Dean had been so helpful these last few days, he wanted to do something to make it up to him. “We should go for dinner after you finish. For real.”

“Are you trying to woo me?” Dean asked with a playful spark in his eyes.

“Thank you, actually,” Castiel answered. “If you are not too tired.”

Dean considered that for a moment. “I know a great place. If you can wait a couple of hours for the crowd to break, I can sweet talk Ellen and get out of here earlier.”

“Deal.” Castiel would need three coffees to keep him going at work the next day, but it was worth it. There was no place he’d rather be at that moment.

An hour and a half later -earlier than he had promised – Dean led Castiel around the Roadhouse, where all the employees parked while working.

“It’s time to meet my baby,” Dean said, walking a few steps ahead.

“You have a baby?” Castiel asked confused. To his knowledge and observation skills, Dean was not married, and he hadn’t mentioned a child before. Of course Castiel couldn’t claim to know a lot about Dean, now that he thought about it, he knew nothing about him other than his name, his work and his LARPing hobby.

“Not that kind of baby,” Dean chuckled as he stopped in front of a black muscle car. He placed his hand on the hood and then announced proudly, “This is my baby.”

Castiel’s knowledge of cars was limited to how often he had to take his own Prius to the garage for service, and his knowledge specifically on classic cars similar to the one Dean owned was zero, but he had to admit Dean’s baby was a beauty. All sleek lines and shiny black metal.

He slid carefully into the passenger seat as Dean took his place behind the wheel.

“What do you think?” Dean asked, eyes full of expectation.

“She is beautiful, Dean,” Castiel said.

Dean ducked his head, but his smile was so big it was hard to hide it. There was pride written all over him, from the way his fingers touched the wheel like it was some precious treasure to his face that was half turned to the side to hide his expression.

He pulled out of the parking spot and ten minutes later they parked in front of a small diner.

The smell of coffee and bacon welcomed them as soon as they stepped inside. Despite the late hour, there were a few customers in the diner, a couple of them sitting on the stools neatly lined in front of the long counter, and a few taking up the booths by the huge windows. A blonde waitress with a checked apron tied around her waist refilled the mugs of three men in police uniforms sitting by the door.

Dean touched Castiel softly on the elbow and led him to the back saying, “I know it looks a little run down, but trust me, they have amazing burgers.”

The laminated menu on the booth they chose advertised a huge variety of foods, but they both ordered a bacon cheeseburger with fries and beers. As soon as Castiel bit into his burger the rich flavor of greasy bacon and juicy beef accompanied by the tangy sauce they used flooded his mouth. It was delicious. From across the booth, Dean watched Castiel’s reaction intently, waiting for his opinion before he tried his own burger.

Castiel used a napkin to clean a drop of sauce he could feel at the corner of his mouth before speaking. “You were right. This might be the best burger I’ve ever eaten.”

“I never said it was the best burger, though,” Dean said, taking a bite from his cheeseburger and closing his eyes to savour it. He swallowed, and then he continued, “I just said it’s really good.”

Taking a sip straight from his bottle, Castiel asked, “What’s the best burger you’ve ever eaten then?”

“I make the best burgers,” Dean boasted with a cheeky grin.

“In your opinion.”

“In everyone’s opinion. Just wait till you try them.”

“You are going to cook for me?” Castiel asked.

Dean shrugged, tilting his beer bottle towards Castiel. “Gotta take care of my fake boyfriend.”

“I’m not your fake boyfriend yet,” Castiel observed, dropping his eyes coyly to his plate. “This is only the first date.”

“I’m confident. No one can resist my charming personality,” Dean chuckled. “My brother used to say I could charm my way out of jail, if I had to.”

“You have a brother?”

“Yeah, Sammy,” Dean said proudly, leaving his burger on the plate to reach for his phone. He tapped the screen and showed Castiel the picture he had as background of him and a taller man with brown hair that fell almost to his shoulders, arms around each other as they leaned against Dean’s baby. “He's a lawyer too, and a damn good one.”

“You must be proud.”

Dean looked down at his phone with a soft expression. “Of course I am. I just wish he hadn’t moved all the way out to California.” He put the phone away and concentrated on his food again.

“Do your parents live in California, too?”

Dean chewed slowly, his face falling. “They are- uh. Gone. Both. Our mom when I was four. House fire. Dad got hit by a drunk driver almost eight years ago.”

Castiel paused with his burger half way to his mouth. “I’m so sorry, Dean. I wouldn’t have asked if I’d known.”

Dean shook his head but refused to meet Castiel’s eyes. “Don’t worry about it. Sam and I still have each other, and we also have our uncle Bobby, so it’s not that bad.”

Castiel reached over the table, grabbed Dean’s hand and squeezed. He hoped this would convey all he wanted to say but didn’t have the words for. Dean looked up surprised, but he didn’t pull away.

“I wanted to be a chef,” Dean said all of a sudden. “Before my dad… well, before.”

“Why didn’t you?” Castiel asked, his hand still around Dean’s.

“I wanted to help Sammy through law school, and Ellen, you know Ellen, she owns the Roadhouse, she offered me a job, and I guess I stuck around.”

“That was very generous of you, Dean.”

“It was the right thing to do,” Dean said. “Sam's a freaking genius. I had to help him.” He paused and then, pulling back his hand to continue eating, Dean said, “What about you, any siblings?”

Castiel’s hand itched to reach over and touch Dean again, but he didn’t. “I’m an only child. My parents were more focused on their careers than creating a family, and one child was enough for them. They moved to England after they retired. I visit them every Christmas, and sometimes in the summer.”

“That sounds fancy,” Dean whistled.

“Trust me, it’s not. It’s a lot of jet-lag and a lot of nagging. But they are family.”

The conversation turned to easier topics after that. Dean described a few of his LARPing adventures with Charlie, which were hilarious. Castiel told Dean the only hobby he had time for was jogging. Dean was appalled at that. Why would any sane person get up earlier to go running? At some point Dean stretched his legs under the table, and his right ankle ended up touching Castiel’s left. Castiel caught himself pressing back, and neither of them pulled away. It was comfortable. They kept talking long after they were both done with their burgers and Dean had ordered and eaten a slice of cherry pie. Before Castiel knew it, he was looking down at his watch and it was almost four in the morning.

“Jeez, look how late it is,” Dean said, peering at the time. “And you have to work tomorrow. Sorry I kept you up.”

“Dean, I asked you,” Castiel said, and when Dean didn’t look convinced, he added, “I had fun.”

As they walked back to the car, Dean bumped his shoulder against Castiel with a mischievous glint to his eye. “So, do I get a second fake date?”

“I believe you do,” Castiel laughed.

Dean ran ahead and held the passenger door open for Castiel, keeping on the joke. “Should I take you home?” Dean asked when he was in the car too.

“I’ve parked near the Roadhouse, so if you could take me back there, it'd be great.”

“Yes, sir!”

The drive back was too short, dark buildings and empty streets blurring together under the yellow street bulbs. It was quiet, just them and the low hum of a rock song playing on the radio. When Dean stopped the car in front of the Roadhouse, Castiel realised he didn’t want to leave.

“I had fun tonight,” Castiel said again and turned to look at Dean. He was watching Castiel with a weird expression on his face, like he was trying to figure something out. Then his eyes moved from Castiel’s eyes to his lips, and Castiel’s heart skipped a beat. His breath caught in his throat.

This was a _moment_ , right? The moment you’d wait for after every first date, where one of the two moves in for the kiss. Would Dean try to kiss him? Did Castiel want him to try?

Dean looked away, and the moment was gone.

“Me too, Cas. We should do that again.”

There was a pinch of disappointment in Castiel’s heart, but then he shook his head and remembered why they were here to begin with. They were trying to make Michael fall for Castiel. He had to focus.

And yet he felt lonelier than ever when he got out of Dean’s car and walked towards his own.

***

“Who’s Dean?”

Meg was sitting cross-legged in his chair when Castiel arrived at the office the next morning. He was too tired to deal with this without at least one more cup of coffee.

“How do you know about Dean?” Castiel grumbled, throwing his briefcase on one of the two armchairs in front of his desk and collapsing in the other.

“Gabriel told Hannah this morning, and she told me while we were making coffee,” Meg said, rolling her eyes, like Castiel should already know the answer. “You hooked up with a barman? I want all the details.”

“No. And get back to work.”

Meg shook her head disappointed. “You wound me, Clarence.” She stood up and walked away, but before she reached the door, she turned around once more. “By the way, have you seen my Cosmopolitan? I can’t find it.”

“No, I haven’t” Castiel answered too quickly, hoping she couldn’t see him sweating from where she stood. Hopefully she didn’t know it was him who had stolen the magazine.

Just to be safe, he hid it among her folders when Meg left with Hannah to grab lunch a few hours later.


	4. Step 4: Spend time with him without pressure or romantic intent

“I don’t get it. I thought I was supposed to make myself unavailable,” Castiel complained, frowning at the menu hanging above the counter.

Dean placed a hand on the small of his back, sending a jolt of surprise to run through Castiel’s spine, until he realised Dean was only trying to make him take another step forward. The line was moving fast, and luckily everyone’s chatter was loud enough to muffle Castiel’s fast heartbeat.

“That’s what you get for taking dating advice from a chick’s magazine,” Dean said, eyes glued to the steaming pie resting on a glass plate by the register. He shifted his weight from one foot to the other impatiently, and their shoulders brushed accidentally. Castiel froze in place.

Since that night at the diner everything was so confusing to him. It was like he was hyper-aware of every move Dean made. Which was insane, because Dean wasn’t acting any different than usual. It was just Castiel reading too much into it. It was Castiel’s fault for spending the last couple of days on the brink of exhaustion, because he couldn’t stop tossing and turning at nights, wondering if he had imagined that _moment_ in the car before he left. Castiel was just confused, right? It was Michael he was in love with, and Dean was just… Dean.

“I’ll get a slice of pie,” Dean declared. “You should get one too. You haven’t had time for breakfast yet, right?”

“I don’t have time for breakfast. I’ll just get a muffin. It’s easier to eat and walk at the same time.”

As the boy behind the counter took their orders and turned around to prepare their coffees, Castiel dared to steal a sideways glance at Dean. He looked the same - bright green eyes, freckles all over his nose, tongue caught between his lips in thought – but to Castiel everything was different.

“This is getting more complicated than I expected,” he sighed.

“You should have confessed like I told you,” Dean said, pushing his hands in his pockets, not realizing that Castiel had been talking to himself. “You can still confess.”

“I can’t confess. I’m supposed to be dating you.”

Castiel should have never lied about that date. His life would have been so much easier now if he hadn’t. Michael wouldn’t think Castiel had a boyfriend, and Castiel would be able to confess, and he and Dean wouldn’t have gone for dinner, and Castiel wouldn’t have this knot in his stomach every time he thought about this whole situation. Michael was the one he had been pining for all these years. What was wrong with him?

Dean brought his hand over his chest in a dramatic gesture and said with an over-exaggerated sad face, “Don’t break my heart, Cas.”

Castiel felt a blush blossoming across his cheeks. Immediately, he turned his face away to hide it, pretending he was looking out the window. What _was_ wrong with him? Dean was obviously just joking. _Get it together Novak!_ He had to stay focused. He had to stick to his original plan, and everything would just fall into place. “What does it mean to spend time without pressure or romantic intent?”

“Isn’t that what we’ve been doing?” Dean said while the barista returned with two cups of steaming coffee, a slice of pie in a box and Castiel’s lemon muffin. Castiel made a move to take his wallet out, but Dean shooed his hand away. “Don’t worry, I got this. What kind of fake boyfriend am I, if let you pay for your coffee?” The wink that accompanied his words really did nothing to help untangle the knot in Castiel’s stomach.

“I’m buying next time,” Castiel said. “So I get half-drunk, tell him I have a secret crush on someone and ask him for his help?”

“It’s the fastest way to a man’s heart, I’m telling you. It worked on me after all.” Dean wiggled his eyebrows at Castiel, ever the tease. “Cas, relax. You know, I don’t think this is good for you. No relationship should be that hard. Maybe you should let it go or take a step back at least,” he added in a more serious tone when his jokes failed to get a smile out of Castiel.

“I don’t know what I’m supposed to do,” Castiel confessed, and those were the most sincere words he'd said that day. Everything was so much easier when he was just minding his own business, crushing on Michael from afar and keeping to himself. This whole thing was getting out of his control, and he had to find the magic plan that would just make everything click into place.

Dean shook his head. This back and forth between them had been going on for almost half an hour now, and it was easy to see how he must have grown tired of it. If there wasn’t a hurricane wreaking havoc inside Castiel’s mind at that moment, then he'd feel sorry for monopolizing the conversation. As it was, all of Dean’s attempts to steer the conversation away from their Cosmo-plan had been fruitless.

“If I were you, I’d find an excuse to go out with him. Like dinner to discuss something you guys are working together on.”

They walked out of the coffee shop, Dean holding the door open for Castiel, who was trying to balance his briefcase in one hand and both the muffin and the coffee on the other. He was already regretting the muffin. There was no way he could eat it on his way to court.

“We are not working on the same case,” Castiel said, leaning against the wall by the door.

“So what? Just ask him to celebrate after you win.” Dean tried his coffee, but it was still too hot. He hissed as it burned his tongue. “Or don’t. You can always come by the Roadhouse, and I’ll give you my employee 100% discount on the beers, and we celebrate together.”

“You are so sure I’m going to win?”

“I was,” Dean said, checking the time on his cellphone, “but if you don’t hurry up, you’re gonna be late.”

Castiel fought with his sleeve, trying to check his watch without spilling his coffee. “Fuck, you’re right. Here, you can have the muffin. We’ll talk later?”

“Sure, text me after you’re done. And go for the pie next time, it’s delicious,” Dean said, waving. Castiel rushed away cursing at himself for not paying more attention to what time it was. Although time passed unfairly fast when he was with Dean, so he really couldn’t be blamed.

***

_< <To: Dean W. 16:48_

_Guess who won even if he was two minutes late today_

_> >From: Dean W. 16:50_

_Congrats! Decided how you're going to celebrate after all?_

The answer was easy. Castiel liked Dean’s idea about beers at the Roadhouse, and maybe if the mood was right, they could go for burgers again, or try something different. Whatever they ended up doing, Castiel was sure he was going to have fun with Dean.

A knock on the door interrupted him before he could reply.

“Novak, I heard you won today,” Michael said, leaning against the door frame, hands in his pockets. He looked so effortless Castiel was sure Meg would bet fifty bucks Michael had rehearsed it in front of his mirror. “Good job. Are you taking your boyfriend out to celebrate?”

That was new. Michael had always been kind of friendly with him, but he had never troubled himself to find out how Castiel’s cases were going, never mind congratulating him for winning.

“Dean is working tonight-”

“That’s a shame,” Michael said, not even bothering to let Castiel finish his sentence. “I guess you are free tonight then. We can go for dinner together, if you want.”

“I-”

Dean had said that Castiel should ask Michael out, and here was _Michael asking him_. Was that a sign that this was his fate? Castiel looked down at his phone where his reply to Dean was already half-typed and then back at Michael. He had been pining after this guy for so many years, and now he had a chance.

But he really wanted to see Dean.

But Dean had said to confess.

“I’d love to,” Castiel said finally.

Michael nodded and smiled at Castiel satisfied. “Great, I’ll see you in a few hours then. Nice tie, by the way.”

Castiel caressed the dark blue tie Dean had picked for him that first day they had gone shopping together. He had insisted it would bring out his eyes, and he was probably right. Even Michael noticed it. After so many years, Castiel was finally getting what he wanted. He had thought he'd have felt happier at this moment, kind of like he was floating and nothing could bring him down, but instead, all he could feel was a giant pit of dread where his stomach should be.

_< <To: Dean W. 19:02_

_Going for dinner with Michael._

He pressed _send_ and stared down at the screen intently, waiting for the reply. Should he have added an emoji? His message felt a little impersonal written in plain black letters with nothing to show his feelings on the matter. Something to show he was excited or at the very least happy and nervous. Τhe nervous part was right, at least.

His door shut and locked with a soft _click._ Castiel looked up to see Meg leaning with her back against the door, arms crossed. “Did I just hear that you and Michael _asshole_ Devine are going out for dinner?”

“Meg, you can’t call him that,” Castiel complained. He was well aware of Meg’s less than friendly feelings for Michael, but he had asked her plenty of times already to at least keep it civil while they were in the office.

“Well, did I?”

“Yes, you did,” Castiel said. “Are you happy now?”

Meg scoffed and dropped herself heavily in the armchair in front of Castiel’s desk. “Unbelievable. I thought you were getting over that douchebag. What about the hot bartender?”

The hot bartender was a topic Castiel really didn’t want to discuss with anyone, even Meg. Especially since minutes were ticking by and there was no new text on his phone. Carefully, so as not to seem as annoyed as he was, Castiel said, “It’s just dinner. As friends. It’s not a date or anything.”

Meg sighed heavily, looking at Castiel from head to toe and judging him, hard. “Sure, Jan.”

Castiel narrowed his eyes at her. “Who’s Jan?”

***

The restaurant Michael had picked had high ceilings, dark walnut, round tables and waiters dressed in crisp white shirts buttoned all the way to their throats in such a way that made Castiel wonder if they could breathe. Dean would have joked that of course they weren’t breathing, because they were little robots, judging from their stiff posture and high noses.

Castiel shook his head. He was not supposed to be thinking about Dean right now.

The menu was full of dishes Castiel could hardly pronounce and exotic ingredients that he'd never heard of before, so he decided to play it safe. Frutti di Mare looked like the best option; it was a dish he had eaten plenty of times before, so he knew he was going to like it, and it was pasta. He couldn't go wrong with pasta.

Michael though, had other plans. “Two scallop sashimi with Meyer lemon confit and… a bottle of pinot grigio,” he said, handing the waiter his menu while straightening down his tie with the other hand. The waiter snatched Castiel’s menu out of his hands before he could protest, and rushed away to pass the order to the kitchen. Scallops it was.

“I hope you don’t mind. I come here very often, and I can assure you, the scallops is their best dish. You're going to love it.” Michael was sitting across from Castiel relaxed, one leg crossed over the other, elbow resting on his chair’s back. He was in his element, and it showed.

The scallops really were good, even if they were a tiny portion that barely suppressed Castiel’s hunger. Maybe it was for the best. After all these years, he was finally out with Michael, and just the two of them, too! Their conversation flowed easily, Michael showing never-before-seen interest in Castiel and his cases and encouraging him to talk and open up. The reality of the situation was finally catching up with him, and now excitement bubbled inside Castiel and made his stomach tingle with all the possibilities that were suddenly laid out in front of him. Even if the portion had been bigger, he didn’t know if he'd be able to finish it.

“He didn’t!” Michael exclaimed, laughing as the waiter refilled their glasses with wine. They were already on their third glass each.

“Nobody believes me when I tell this story. I should have taken a picture as proof.” Castiel felt warm and relaxed. He could talk with Michael for hours and hours.

“He actually walked into the court wearing his ex wife’s wedding dress?”

Castiel winced at the memory. It was side-splitting to recall now, but he'd almost had a stroke that day. Needless to say they'd lost the case. “It was an ugly divorce.”

Michael snapped his fingers together, a thought lighting up his face. “Now I remember. Gabriel reached out to the ex-wife for a settlement after the wedding dress incident, didn’t he?”

“He did. I can’t say I was disappointed.” Castiel would have settled from the beginning if he'd known just how far his client could take things just to make a point. “I’m lucky he found the whole situation hilarious. Other people would have fired me for not making sure the client was dressed appropriately.”

“You and Gabriel, you are friends, right?” Michael asked, swirling his wine.

“I guess,” Castiel said and then quickly added, “but he’s never been favourable with me over anyone else. Business is business.”

“But it certainly doesn’t hurt your career,” Michael noted.

“Gabriel would never-”

Michael cut Castiel off with a wave of his hand. “Relax, Castiel. I didn’t mean it like that. After all, you always said you're not interested in becoming partner.”

“I’m not,” Castiel said quickly. It was like he'd said to Meg so many times already. He didn’t need the promotion, and he didn’t care for the bigger salary. Not to mention Michael was top contender for the position anyway. There was no arguing that.

Michael took a sip from his wine, his eyes never leaving Castiel’s. “You know, Castiel, I wonder why we’ve never done this before. I think we have… chemistry.”

Castiel could almost hear angels singing and shining their holy light upon him. Michael thought they had chemistry! The plan was working.

“Your boyfriend is a lucky guy,” Michael continued. “How did you two meet again?”

Sticking as close to the truth as possible, Castiel said, “We met at the Roadhouse. On Gabriel’s birthday, actually. I went to the bar to order a drink, and the rest is history.” Of course he made sure not to mention exactly what that history entailed. The question about the girl Michael had left with that night burnt at the back of his mind, but he bit his tongue and kept his mouth shut. This was going well, and Castiel didn’t need to destroy it with his big mouth.

Tilting his head to the side, Michael pursed his lips. “So you went for a beer and left with his number?”

Castiel shrugged, trying to look as casual as possible. “They say love tackles you when you least expect it.”

Michael nodded, tapping his fingers against the table. “He seems like a nice guy. But I have to admit I’m surprised someone like you would go out with someone like _him_.”

Castiel’s blood instantly ran cold. Michael’s expression had not changed, but there was an edge to his voice when he referred to Dean that was decidedly offensive. Like Dean was inferior to him. “What do you mean?”

Resting his chin against his palm, Michael gave Castiel a small smile. “Oh, nothing bad,” he said. “He is easy on the eyes, but he is just a barman.”

“Dean is a great guy. Funny too, and with a big heart. He wants to be a chef,” Castiel said, his voice steady through all his inner turmoil. Dean was so much more than just a barman. He was kind and loving, and he always had a witty reply or anecdote to lighten the mood and make Castiel smile. He sent Castiel texts throughout the day to check on him and would even sometimes share pictures and tidbits about his day just to make Castiel forget about all the things troubling him. Michael had no idea what he was talking about, and the fact that he wore more expensive clothes and had a more prestigious job didn’t give him the right to judge Dean.

“A chef? Well, he better hurry up, how old is he? Thirty?” Michael wondered and Castiel felt numb. The room was suddenly too cold and yet too hot, and his mouth felt dry. How was he supposed to say that thirty isn’t even that old, and just because Michael was already a successful lawyer at thirty-five not everybody else should be the same? He could taste the words on his tongue, but they remained stubbornly stuck there. Frozen beyond his power.

He was saved from having to answer by the waiter, who came to ask if they wanted dessert.

“No, thank you,” Castiel said, interrupting Michael before he could make a sound. “Just the bill.”

His blood was thrumming against his temples. Just a barman. That’s all Michael saw in Dean without even taking the time of day to learn more about him. He could throw up.

Michael side-eyed him but kept his mouth shut, probably sensing that he had crossed some kind of line.

The seconds passed excruciatingly slow as Castiel watched Michael drone on and on about his new case, and how it was like he'd already won. The check couldn’t come fast enough, and when it did, Castiel threw his half of the bill on the table and left as quickly as he could. He found himself on the street, one arm through his trench coat’s sleeve, the other half of it dragging behind him. His hands were shaking. Thank God he had driven there with his own car and didn’t have to ask Michael for a ride back to the office. Truthfully, he didn’t want to spend another minute in Michael’s presence while his skin was still vibrating with irritation.

Slamming the door as he got inside the car, he rested his head against the wheel and took deep breaths. Tonight was a disaster. There was no arguing that. Everything had started out fine, and Castiel had thought that he'd finally have his chance, but when Michael had said all these things about Dean…

_I’m surprised someone like you would go out with someone like him._

Like him. Like they were so much better, and Dean was just some poor guy that should feel thankful just to work where Michael frequented. There was no other way to interpret his words.

And they were wrong. So fucking wrong.

Would Castiel be an asshole if he called Dean that moment and asked him to do something together? He knew it was selfish, but he needed something to cheer him up and make him forget; and Dean, easy-going, kind, always smiling Dean could help him.

A weird thought occurred to him then. Dean had never answered the text Castiel had sent him earlier about going out with Michael. That couldn’t be, Dean always answered. Maybe Castiel hadn’t noticed. Taking his phone out, he saw that yes, Dean really had sent a text that Castiel hadn’t noticed. But it was only a thumbs up emoji. Castiel tried not to let his disappointment get the best of him. It was possible Dean was just waiting for him to call and tell him all about how the night went. Should he call? A glance at the time said decisively no. Dean was still at work, and it might get him in trouble if Castiel called out of the blue.

With a sigh, Castiel turned the key in the ignition and started on the way back to his apartment.

***

Castiel had just enough time to brush his teeth and get dressed before he had to leave for work. He had closed his eyes for just a second after turning off his morning alarm and somehow he had fallen asleep. If he didn’t hurry up, he was going to be late, and he had an appointment with a client first thing in the morning.

_< <To: Meg M. 07:17_

_Please get me coffee!!_

It had been an awful night. After everything had gone wrong at his dinner with Michael, Castiel had returned home only to be too strung up to fall asleep. He'd spent the whole night staring at the alarm clock at his bedside table, waiting for the sleep that was eluding him. He must have fallen asleep at some point, but he couldn’t have slept more than three or four hours. Castiel felt – and looked – terrible, with a thrumming headache and dry throat, not to mention how he could barely keep his eyes open. This was going to be a hard day to get through.

While he was waiting for a taxi to come and pick him up – he was not driving to work, he wasn’t – he thumbed his phone in his pocket. Before he could talk himself out of it, he took it out, scrolled through his contacts until he found Dean’s name and pressed call.

Beep beep beep beep.

No answer.

Dean could still be sleeping, though. Of course Dean was still sleeping. He had worked until pretty late last night, it was not like he had to be up as early as Castiel. Dean would probably call him back when he woke up, wouldn’t he? He hadn’t called after he'd finished his shift last night, even though he must have seen Castiel’s missed call. And he hadn’t texted either.

<< _To: Dean W. 7:28_

_Coffee today? Or lunch?_

Castiel put his phone back in his pocket, feeling better and sure that he would get an answer as soon as Dean woke up. The answer came much faster, though. As a matter of fact, it came exactly two minutes later.

_> >From: Dean W. 7:30_

_Sorry, busy today._

Oh.

So Dean had seen the text but hadn’t answered his phone? And he didn’t have time to see Castiel at all today? Not that it mattered, Castiel didn’t expect Dean to always be available when he asked. He was sure Dean had something important to do and would reschedule. Maybe for tonight or tomorrow. Castiel stared at his phone for all of the twenty minutes the drive to the office took, but no new messages arrived.

With his eyes still glued to his phone screen, Castiel never saw Meg coming for him as soon as he stepped his foot out of the elevator. Meg tackled him and dragged him to the photocopy machine, pushing him inside despite all his protests and fighting. With her back against the door, she smirked at Castiel and locked the door with a soft _click._

“Meg, what are you doing? The client’s probably waiting for me already.” Castiel really needed to get it into her head that she was his assistant and not the other way around.

“The question is what are _you_ doing, sweetcheeks?” Meg crossed her arms over her chest, her brows furrowed together as she stared Castiel down.

“What are you talking about? You locked me in here and now I’m even more late to my appointment,” Castiel protested.

Meg took a couple of steps towards him, and unconsciously, Castiel took two steps back, until his ass hit the photocopy machine. He was trapped, and Meg’s expression could only mean trouble for him.

“You are more faithful than a puppy,” Meg said. Castiel jumped a little, startled at her accusing tone. One would think that being faithful would be a good quality. Meg took another step forward, but Castiel had nowhere to go except climbing up the copy machine, and he was not that desperate. Yet.

“If you were really dating that Dean guy-” another step “-you would have never gone on a date with Michael.”

“It was not a date.” Castiel felt like the room was too hot and constricting, and Meg was almost pressed against him. He loosened his tie, trying to get some oxygen inside him, but it was a futile effort. “It was just dinner,” he tried again, hoping that just wishing and lying would get her off his case and out of this tiny room. “Just two colleagues hanging out without any pressure or romantic intent.”

Meg’s eyes shone with triumph. “That’s a direct quote from Cosmo.”

Fuck. Castiel had slipped up and given her the evidence she wanted, served on a silver plate.

“Caught you red handed.”

“I plead innocent,” Castiel said as she leaned closer to him, like a bloodhound sniffing the fear on her prey.

“Overruled.”

“Meg-”

“You are following the Nine Steps Out Of the Friendzone article.” Meg pressed her finger against his chest, and she was so close Castiel had to stand half-laying over the copy machine to keep a sliver of personal space between them. “Admit it,” she hissed.

“Meg, I think you’ve been watching too many conspiracy videos lately,” Castiel said in one last desperate attempt to keep his dignity.

“You somehow convinced that Dean guy to help you, didn’t you?” Meg continued as if Castiel had never said a thing. “Come on, Clarence. Don’t lie to me. I know you better than your own mother.” Meg placed both her arms on the copy machine, trapping Castiel between them. Εven though Castiel was a good deal taller and stronger than her, he suddenly felt like she could crush him just on the power of her stare alone.

He opened his mouth to protest, but it came out all wrong. “So what if I am.”

In an instant, Meg was standing on the other side of the room again, her hands clasped in front of her. “Wonderful,” she said in a sing-song voice. Somehow this happy version of her was even more terrifying. “I want in! Tonight, you, me and your fake boyfriend.” She unlocked the door, tossing her hair back as she walked away.

“And don’t try to run away,” she warned over her shoulder.


	5. Step 5: Flirt with him

Castiel had spent the whole day in an emotional turmoil. On one hand he really wanted to go by the Roadhouse and see Dean, because as the day wore on, he got more and more worried that he had done something to piss Dean off, and that was why he was not answering Castiel’s calls. Of course, what Dean had texted him could very well have been the truth. Dean could have been busy these days and just didn’t have time to tell Castiel. On the other hand, the thought of going there with Meg sent shivers down his spine. Meg was just as likely to spend the whole night getting drunk as she was to give Dean the third degree, and truthfully, Castiel was not sure which of the two options was the worst.

The one bright point was that his new case was big. No, it was huge. When he had briefed Gabriel, after the meeting with his new client, his eyes had almost turned to dollar signs.

Imagine Andrew Gallagher going for his annual check up with Dr. Adler, leaving with a new prescription and a few days later ending up in the ER with troubles breathing. Allegedly caused by the new drug he was on. And all the doctors that had seen him since had been confused as to why Gallagher’s prescription had been changed, since his test results had barely shown any problem at all. Maybe an indication, but nothing that would make them prescribe the new drug. What a case! Gabriel had sniffed the huge amount of money they could win, if they could prove medical malpractice, even before Castiel had finished briefing him. But there was a lot of work to be done before they got there. Adler’s patients and other witnesses to be interviewed, background checks, test results to be collected, professional opinions to check everything again. Castiel could already see all the endless hours and sleepless nights that were waiting for him.

Running on four coffees and very little sleep, Castiel was dragged by Meg to the Roadhouse almost the same instant she was off the clock. Dean spotted them as soon as they walked in, but they were too far away for Castiel to see his expression. He was behind the bar, speaking to two men in business suits who were laughing at something he was telling them. Meg walked straight to the bar, Castiel practically running behind her to keep up.

“Good evening.” Dean gestured at the empty bar stools in front of them with a smile that didn’t reach his eyes. That was definitely a bad sign.

  
“Hello, Dean,” Castiel said, taking a seat. Dean was pretending to be busy cleaning a wine glass, but he did nod, acknowledging him. “I understand you’ve been busy these days,” he added after much debate with himself.

  
The guilty glance Dean sent his way confirmed what Castiel knew all along. Dean was avoiding him on purpose.

  
“Yeah, sorry about that. My brother’s in town.” To his credit, Dean really did look like he was sorry, but that didn’t explain the radio-silence.

  
Meg, who until then had been watching them in silence, elbowed Castiel at his side, smiling at him in a way that clearly said,  _introduce me._

  
Castiel rolled his eyes but obliged her. He wouldn’t get a moment to speak with Dean in peace unless he did. “Dean, I want you to meet Meg, my assistant. Meg, this is Dean.”

  
Dean extended his hand with a guarded expression, his eyes flickering between Meg and Castiel for a second before he closed the gap. Meg, ever comfortable in uncomfortable situations, shook Dean’s hand with confidence. “A pleasure.” She gripped his hand in hers tightly, unabashedly checking Dean out from where she stood. “I see Clarence has a good taste in fake boyfriends.”

  
“Meg!” Castiel shook his head in disbelief as Dean stood there with his mouth hanging open uselessly. She was truly insufferable. Castiel should have never let her convince him to come to the Roadhouse together. Not that he had ever stood a chance of refusing.

  
Catching a piece of hair and twirling it through her finger, Meg shrugged. “What? It’s true.”

  
Dean, recovering much faster than Castiel, grinned ear to ear at her. “You are drunk-make-out-and-throw-up-on-New-Years-Eve Meg.”

  
“My reputation precedes me, I see. Clarence, you disappoint me. That story isn’t even the most fun one,” Meg said, dropping her hands on the bar top. “I’ll have a vodka cranberry.”

  
“Bossy.” Dean narrowed his eyes at her, but he grabbed a Smirnoff bottle and started preparing her order. Without being told to, after giving Meg her drink, he placed a glass of beer in front of Castiel. Stubbornly, no matter how much Castiel tried to catch his eye, Dean kept looking everywhere but at him.

“I hope it’s up to your standards,” Dean told Meg in a challenging voice.

  
Fluttering her eyelashes at him, Meg brought the straw to her mouth and took a sip. “Well, you tried your best.”

  
"Next time, I might add some of my spit. Really gives it a rich flavour,” Dean said without missing a beat, and Castiel couldn’t tell whether he was joking or not. He had never seen him getting upset before, and especially at a customer, but Meg had that effect on people. She hadn’t exactly been a ray of sunshine since they arrived.

A man passing behind them chuckled at the exchange as he took the seat on the other side of Meg. He was tall, with dark hair that were on the long side. Castiel had to do a double take, because he knew that man. Or at least he had seen a younger version of him smiling brightly from Dean’s phone wallpaper. Sam Winchester really was in town.

“If Ellen hears you talking to a customer like that, she'll serve your ass for Sunday lunch,” the younger Winchester joked, grinning from ear to ear.

“Sammy-”

“And who might you be, friendly stranger,” Meg jumped in, immediately turning towards Sam.

“Sam Winchester,” Sam said at the same time Dean said, “My brother.”

“Meg Masters. Are you a bartender, too, Sam? Because I’m sure I’d enjoy your cocktails more than your brother’s.”

To his credit, Sam didn’t seem fazed by Meg’s very forward way of speaking. Castiel admired him for that. “A lawyer, actually.”

Fingers playing with her straw, Meg eyed Sam with appreciation. “Well isn’t that a coincidence? I happen to think lawyers are super sexy.”

Castiel groaned, wishing the earth would miraculously open up and swallow him whole, while Dean grabbed her from the shoulder and turned her towards him. “Hey, claws off my brother, lady.”

“Dean, it’s fine,” Sam said, laughing, and then turned to Meg. “I’m sorry. You seem like a very… uh… passionate woman, but I’m engaged.”

“Shame, we could have had a lot of fun.”

Finally, Dean turned to Castiel, leaning forward and stage whispering. “Dude, why are you letting her out without a leash?”

Castiel winced. “I promise, she is usually not that bad.” At least Dean had remembered he existed.

“Are you guys Dean’s friends?” Sam pointed at Meg and Castiel, brows furrowed.

“Excuse me, I should have introduced myself. Castiel Novak.” Castiel offered his hand immediately, and Sam took it, his eyes suddenly shining with interest.

“Castiel? You are Cas?”

“I am,” Castiel said confused. First Charlie and now Sam. Had Dean told everyone about him? More importantly, _what_ had Dean told them about him?

“Oh my God! You are all Dean is talking about these-”

“Sammy!” Dean exclaimed, face burning red.

“He’s been telling you good things, I hope,” Castiel said carefully.

“The best, I promise. I was actually looking forward to meeting you while I was visiting,” Sam said with a friendly smile.

“Jesus, Sammy. You are engaged, don’t go around picking up random dudes from the bar,” Dean joked weakly, all previous anger at Castiel seemingly forgotten. He was acting so weird, Castiel was starting to get worried. Maybe coming to the Roadhouse wasn’t a good choice after all. Maybe he should have tried to meet Dean somewhere more private and not where his brother, Castiel’s assistant and all of Dean’s coworkers could hear them.

The upside of coming with Meg, was that Meg was not easily persuaded to back off when she found a new potential chew toy, and especially not by such trivial things as girlfriends and fiances. When she jumped in, all witty jokes and sharp tongue, even Dean couldn’t interrupt her conversation with Sam. As it turned out they had a lot of things in common, not the least of which was their obsession with serial killers – _‘No, no, no, you have it all wrong, that was the Butcher of Rostov’_ and ‘ _What was the name of that guy that ate his father’s heart?’_

Castiel tried really hard to tune them out. He really didn’t need the image of someone cooking, or worse _eating_  a human heart.

Dean turned his back to them as much as possible, visibly shuddering. “God, they are disgusting.”

Castiel leaned over the bar and said in a low voice, hoping only Dean would hear, “I really am sorry about Meg. She is… an acquired taste.”

Dean winced at that, nose wrinkling. “Yeah, count me out. What are you guys doing here anyway? Don’t you have another date with Michael?”

“It was not a date,” Castiel said for the hundredth time that day. “And yesterday was a disaster.”

Dean straightened up at that but kept his expression carefully neutral. “What happened?”

 _Oh, you know he just said some awful stuff about you, and then I ran away with my tail between my legs._ Yeah, Castiel was not saying that to Dean. Even if he was tortured, he was not going to repeat Michael’s words.

For a lack of a better answer, Castiel shrugged.

Dean lowered his eyes, fingers playing nervously with a button on his shirt. “Was he not interested in you?”

“The problem is,” Meg cut in, her own conversation with Sam on hold for the sake of spying on Castiel’s conversation, “that Clarence sucks at flirting. I swear, if I don’t set him up with someone, he can’t do it on his own.”

With a cocky, lopsided grin, Dean patted Castiel on the shoulder. “I don’t know, he looks pretty fucking good to me.”

With an undignified sound, Sam choked on his beer, coughing and wheezing, his face a bright red color, thankfully making everyone turn to look at him, and so they didn’t see the way Castiel turned bright red himself for completely different reasons.

“Shut up, Sammy,” Dean barked, throwing a towel at his brother to clean up. “Jesus, look at the mess you made.”

While Dean and Sam cleaned everything – ‘ _I swear you’re worse than a toddler’ ‘It’s your fault jerk!’ ‘Shut up, bitch.’_ \- Meg watched them with her fingers tapping against the wooden bar, deep in thought. Then something clicked, and she brought her drink to her lips with a sly smile so brief, that if Castiel hadn’t been watching her to see if she caught him being flustered over something Dean said, he would have missed it.

“Dean, you are not being paid to babysit your brother.” A short blonde Castiel remembered seeing serving tables from time to time came behind the bar, hands on her hips. “Get back to work.”

“If I was being paid to babysit my brother, I’d be a millionaire by now and wouldn’t have to work at all,” Dean said with a hint of amusement to his voice as he poked her at the sides.

“Dean Winchester,” the blonde said, slapping his hands away. “It’s a busy night. There are customers waiting for you.”

“Alright, alright, jeez.” Dean walked to the other side of the bar, the blonde waitress right behind him as she tied an apron around her waist. Castiel had never paid much attention to the bartenders of the Roadhouse before he'd met Dean – he interacted much more with the waitresses – but he was fairly sure she was the only woman he had ever seen behind the bar.

“That’s Jo.” Sam leaned on his barstool to look at Castiel. “She’s Ellen’s daughter.”

“Ellen is the owner, right?” Castiel could remember Dean mentioning her name a couple of times in passing, like that night he got off early, and another time he'd been complaining about something, but he had never mentioned any Jo.

“She’s a family friend,” Sam said, drinking his beer straight from the bottle. “She’s known us since we were both in diapers.”

Castiel took that information in, his eyes following Jo as she worked, that night acting as an extra bartender apparently. She was slim but with an athletic figure, her black pants hugging her curves in all the right ways. Quite a few men sitting at the bar kept stealing glances at her as she walked to and fro, serving drinks and joking with the customers. She and Dean moved around each other comfortably, like they had been doing that for years. They probably had. Dean’s eyes were always soft when he looked at her.

“I can’t believe my luck meeting you here tonight,” Sam said. “I’ve wanted to meet you ever since Dean first mentioned you.”

Castiel turned around, frowning. Meg was drinking her vodka, arms folded on the counter in front of her. “Really?”

“Yeah, you seemed like an interesting guy.” Sam shrugged, and then, opening his arms, he added, “Look, I hope this is not too forward, but I was hoping we could talk. I have a few questions, if it’s not too much trouble.”,

“Questions?”

“Nothing bad, I promise. I’d call it… professional more than anything else.”

“I’d be happy to answer them for you then,” Castiel replied, ignoring the side-eye Meg was giving him.

It really was a very busy night, and Dean was rushing from one side of the bar to the other, barely having time to ask them if they needed anything else. At least his mood was a lot better than when Castiel had first arrived. Meg got bored of sitting at a bar quickly - ‘ _I can’t even drink, Clarence, because I have to drive back home, and your bartender is ignoring me’ -_ and Castiel got up to leave with her, after making plans with Sam for the next day.

Maybe it was because he was exhausted, or maybe it was because he wasn’t upset like the previous night, but he slept peacefully all night.

***

The contract he was going over was fairly straightforward, but Castiel still wanted to make a few changes for the best interest of his clients. Said clients, a Mr. Spangler and a Mr. Zeddmore who had just gotten an offer for an advertisement deal through their Youtube Channel, were fidgeting in their seats while Castiel wrote notes over the contract they had been given.

“Mr. Novak, someone’s here for you,” Meg said, sticking her head in through the half opened door. Her voice remained professional, as always when she was in front of clients, but there was a glint of mischief to her eye that had Castiel worried. What had she cooked up again?

“Thank you, Meg. We are almost done here.”

Twenty minutes later, Castiel was shaking Mr Zeddmore and Mr Spangler’s hands – ‘ _oh, no! Please call us Harry and Eddie, man._ ’ – and showing them to the door of his office, when his eyes landed on the _someone_ waiting for him, sitting at the edge of Meg’s desk.

“Hey, babe.” Dean looked up from where he and Meg had been having an intense stare down, the word ‘babe’ rolling off his tongue so easily, Castiel almost forgot to be stunned. Almost being the keyword.

The image of Dean Winchester perching on the edge of a desk in his old leather jacket and hair spiked was such a contrast to everything else around him that Castiel stopped dead in his tracks, mouth hanging open. Lawyers, assistants, and clients in their suits and expensive shoes rushed around them like bees in the beehive, a few of them stealing a glance at Dean, but Castiel could hardly pay attention to any of them.

The smile on Dean’s face faltered. “Surprise?”

“I’m sorry.” Castiel shook his head, clearing his thoughts. “I wasn’t expecting you. What are you doing here?”

“Brought you a snack.” Dean lifted a box from Meg’s desk and a Starbucks coffee with his name spelled as ‘ _Catel’_ inside a black heart _._ “I thought you might need a break.”

“I already had a bagel,” Castiel said. Then, because Dean’s face fell, he quickly reached for the coffee. “Thank you. I’ll save it for later. Catel?”

Dean stood up, rubbing the back of his head. “Sorry about that. It didn’t occur to me the Starbucks guy wouldn’t know how to spell your name until after he had prepared the coffee. I asked for his pen to add a personal touch, though.” He gestured at the heart around Castiel’s name, and Castiel felt warmth travelling from his core to his toes. The closest any of his exes had come to such a gesture was to wait for him outside the building to go for dinner together, and here was Dean, not even his real boyfriend, and he'd dropped by just to bring him coffee.

“Thank you,” he said again and then gestured towards his office. “Come in.”

Meg, resting her face on her hands, winked at him. “Leave that box for me, won’t you, sweetcheeks?”

“Hey, hands off.” Dean made an ‘I’m watching you’ gesture at her as he walked backwards into Castiel’s office.

“Look man, I feel like I need to apologize,” Dean said after the door was closed behind them and they were alone. He walked around, inspecting his surroundings. He looked at the bookcases that lined the walls, and the leather armchairs and picked up the only photo that Castiel had in his office, one taken right after his graduation with his parents. “I didn’t mean to ambush you.”

“You didn’t,” Castiel said immediately, and then, because Dean didn’t look convinced, he added, “I promise.”

“It was Meg’s idea,” Dean said, putting the photo back where he found it. “She said it’d look good for your boyfriend to drop by. I thought you were in on it.”

“I wasn’t, but thank you all the same.” Despite being Meg’s idea, Castiel still thought it was sweet that Dean had agreed and made time to come.

“Please.” He gestured towards one of the armchairs, feeling a little awkward for saying the exact same thing to Dean he did to all his clients. He ought to get a sofa for his office, something that didn’t scream ‘lawyer’ the minute you saw it. Somewhere where he and Dean would be able to sit together like... friends. Friends was definitely the way he wanted to finish that thought.

Dean looked at the armchair but remained standing, his attention now focused on the neat piles of paper on Castiel’s desk and all the little decorative pieces resting there.

“Oh, I saw your boss while I was waiting for you,” Dean said, touching with his finger the nose of a glass deer a client had brought Castiel as a gift. “Both of your bosses, actually. Chuck seems like a cool dude.”

“What did he say?”

Dean waved absentmindedly a hand. “The usual. How do I like working at the Roadhouse, how did we meet, do I like cat gifs?”

“Oh no,” Castiel groaned, rubbing a hand over his face. “Did he tell you about his cat blog?”

“He did,” Dean confirmed, turning around to lean on the desk, hands resting on either side of him. “Right before Gabriel showed me photos from the trip the two of them took to Las Vegas last summer. Say, how did these two ever become successful?”

“Don’t judge a book by its cover,” Castiel laughed. “Chuck only takes on a couple of cases a year, but he is the best, and Gabriel may not look like it, but he is truly scary when he is in front of the judge. These two can drill a witness until he cries without breaking a sweat.”

Dean dragged his finger on Castiel’s desk, creating random circles and lines. Castiel once again was surprised at how two completely separate parts of his life had collided so easily. He’d never thought he’d see Dean sitting by his desk or touching the contracts he had written, but here he was, lashes illuminated by the strips of light that made their way through the shades on the windows, legs loosely crossed at the ankle. It was not a bad image at all.

“Can I ask you something?” Dean said, breaking Castiel out of his daydream.

Castiel raised his eyebrows at him. “I believe you just did.”

Dean looked up, head tilted to the side in a silent _haha, very funny._

Castiel shrugged apologetically, taking a few steps towards Dean, until they were standing side by side, Dean’s back to the desk, Castiel facing it. He closed his hands in fists then opened them again, drummed his fingers against the wood, realized it was a sign of nervousness and pressed his hand down, palm flat. “Ask away.”

Dean chuckled, rubbing a hand over his mouth all shy all of a sudden. “Just wondering, if you wanted to go for lunch.”

“Oh,” Castiel said and then winced. “I already have plans.”

It was a shame, because Castiel really, truly wanted to go with Dean, but he couldn’t cancel.

Dean laughed, shaking his head. “Michael?” There was a hint of bitterness to his voice, a tightness to his mouth that Castiel would have missed if he wasn’t paying extra attention to his reaction.

“Sam, actually.”

A beat.

“What?”

“I made plans with Sam yesterday. He said there are a few things he wants to discuss.”

Dean blinked once and then burst out laughing, this time for real, shoulders shaking, nose wrinkling. “Well damn. My little brother is stealing my fake boyfriend.”

“He is not that little,” Castiel pointed out.

“No, he's a giant moose.”

“We could reschedule our lunch for tomorrow,” Castiel said. “If you are free.”

“Sure let’s do it tomorrow. That way you’ll know that Sam is a giant nerd and I-“ Dean raised his hands to point with his thumbs at himself “-am definitely the funnier brother.”

Castiel bumped his shoulder against Dean’s, biting down a smile. “I knew that already.”

“Yeah?”

“Sure. The more handsome, too,” Castiel said before he could stop himself.

Dean’s eyes widened in surprise, making Castiel’s stomach tighten with worry. Had he crossed a line? He could still take it back and brush it off as a joke. Dean though, recovering faster than Castiel, leaned in, his face just a breath away from Castiel’s.

“And Meg says you don’t know how to flirt.”

Dean’s voice was low, intimate. Something only for Castiel to hear. It sent shivers down his spine, made his heart pound loudly against his ribs and his toes tingle. Dean licked his lips, and immediately Castiel’s eyes fell to follow the motion. It would be the easiest thing to lean in, and he had a suspicion that Dean would let him.

“Cassie, keep your door open while you live under my roof.” Gabriel burst into the office without knocking, Dean and Castiel springing apart like they had been burned. “Oh my God, I was just joking, I didn’t know you two were _actually_ making out.”

Castiel pinched the bridge of his nose, face burning with shame. “We weren’t doing anything.” That was kind of the truth. They were just standing near each other, close enough for their breaths to mingle, noses almost touching, Castiel feeling lightheaded. If Gabriel hadn’t walked in, what would have happened?

“I just wanted to go over some things about the Gallagher case.” Gabriel looked from Castiel to Dean and back to Castiel. “But I can come back later.”

“I was just leaving,” Dean said, and Castiel wished he could touch him and make him stay, but he had to go over the files Gabriel had brought, finish up the Zeddmore-Spangler contract, have a look at the list of witnesses for his upcoming court and still make it to lunch with Sam.

“I’ll see you tomorrow?” he asked Dean, hesitating before putting a hand to his shoulder.

“Wouldn’t miss it for anything.”

“Oh, you two are so cute,” Gabriel cooed, hiding his smile behind the folder he was holding. “I feel guilty for stealing you away now, Cassie. Go ahead, kiss goodbye as if I wasn’t here.”

Castiel froze in place and turned to Dean with panic written all over his face. Dean looked unsure for a second, his eyes searching Castiel’s face for something. Was it guidance? Permission? Then he grinned and he took a step towards Castiel, leaning in. Instinctively Castiel pressed his eyes closed, anticipation rushing through his veins when he felt Dean’s breath against his skin. Then a soft brush of lips against his cheek, and he opened his eyes to find Dean a respectful distance away from him again.

“I’ll give you a better one in private. Have a nice day,” Dean said, raising two fingers to his forehead in a quick salute to Gabriel before winking at Castiel and leaving. Castiel heard Meg’s voice rise in a challenging tone, but Dean’s answer was lost as he closed the door.

“Boo, you guys are prudes,” Gabriel complained, taking a seat in front of Castiel’s office and opening the folder in his lap. “Okay, let’s get down to business.”

***

The Ciel was advertised as a gastronomy bar. It was one of those places that seemed to spring up like weeds everywhere, with exposed brick walls, woven basket light fixtures and long industrial tables, their sides separated by long, horizontal planters in the middle. In truth it was a glorified cafe/bistro that offered brunch at all times of the day. Castiel had often wondered what was the point of calling it brunch if you were eating it in the evening.

He found Sam already waiting for him inside. They ordered something to eat, a kale salad for Sam – funny how Sam and Dean had completely opposite taste in food - and a honey mustard chicken sandwich for Castiel, their conversation flowing so naturally that Castiel felt like he knew Sam for years. In a weird way he did know him. Sam had the same smile as Dean, and a similar sense of humor, but where Dean was open and sharing, Sam kept a polite wall between them.

“You’re moving here? When?” Castiel asked, a piece of sandwich half raised to his mouth.

“Hopefully after the wedding,” Sam said, mentally calculating how long that was. “In seven, eight months time.”

“Dean must be excited.”

“I haven’t told him yet.” Sam frowned, biting his lower lip. “I want to secure a job here before we finalize the move. That’s what I wanted to talk to you about. I had an offer to work at Harrington & Roche. I wanted your opinion on them before I made a decision.”

“They are an excellent firm.” Castiel placed his sandwich back on the plate, wiping his hands with a napkin. Then he reached in his pocket and found a pen. “One of my close friends actually works there, his name is Balthazar. He is probably a better person to talk to than me, but I think it’s an excellent opportunity for you. I can give you his number.”

“That would be awesome,” Sam said, grinning widely. He accepted the card Castiel wrote the number on and then tucked it carefully in his wallet. “Thanks, Cas. That means a lot.”

“You are welcome, Sam.”

“I’m lucky you and Dean are friends. Otherwise I don’t know how I would have gone about this.” He glanced up at Castiel, weighing him with his eyes before continuing. “You and Dean are friends, right?”

Castiel tilted his head to the side, considering the question. He thought it was obvious he and Dean were… friends. “Of course, Sam.”

“Just because, you seem like a great guy, but Dean gets attached easily-”

“I don’t understand.”

“Look-” Sam raked a finger through his hair, “- I know about your plan. All I’m asking is-”

“Sam,” Castiel took a breath, not believing he even had to say these words. “Dean is my friend, it doesn’t matter how we met or what our plan is. We are friends.”

Sam nodded, and Castiel hoped he believed him. “Okay. That’s good.”


	6. Step 6: Make him do things for you

Meg had kicked her legs up on Castiel’s desk, crossed at the ankle, as she read through the file she was holding. Her head was resting on her hand, eyes bloodshot and barely open.

Castiel, in his own effort to stay awake, was pacing the room, dragging his feet from one corner to the other, letters jumping and dancing in front of his eyes. He paused, rubbed a hand over his face and tried again. It was useless. He had been reading the same sentence for five minutes and still couldn’t understand what it said.

“God, it’s two a.m.” Meg rubbed the back of her neck in an effort to fight off the stiffness that inevitably followed sitting in the same position for so many hours. “How many more documents do we have to go through?”

Castiel glanced at the piles and piles of boxes littered around the room. “I’d say we are three fourths of the way there.”

Meg dropped her head back, pressing her eyes closed. “I need a break.”

“Maybe we should just call it a night.” Castiel dropped the folder he was holding on top of the ‘to review again’ pile he had on his desk and then fell heavily on the armchair across from Meg. “My brain is fried.”

Meg opened one eye to look at him. “We have to finish reading all that by tomorrow, and then we have to go over the files of the patients whose profiles fit our case. And then we have to find a connection between Adler and Holy Hosts Pharmaceuticals.”

Castiel groaned, half turning so he could pretend he was comfortable.

“Don’t be a baby. If we take this to court it might be the biggest case of our careers, but we have to convince the judge that we have a case first,” Meg continued, reaching for her cup of coffee and tilting it over her open mouth in a failed attempt to get the last drop.

“But it’s obvious! Gallagher got the prescription and ended up in the hospital less than twenty four hours later.”

“With an allergic reaction,” Meg said. “Which is rare but an already known side effect. We have to prove that Adler had no reason to change Gallagher’s prescription to begin with. We have to find similar cases and find at least one doctor willing to testify.”

“I know, I know. I’m sorry, I’m just tired.”

“Look, we’ll take a five-minute break and then we continue. I’ll get us fresh coffee.” Meg, with inhuman strength that Castiel was envious off, stood up and took both their cups in her hand. Barefoot, because she had kicked off her heels into their second hour of reading, she padded across the room and out of the door.

The next thing he knew, Castiel was being shaken awake and a hot, fresh cup of coffee was being pushed in his hand. He didn’t remember falling asleep at all.

“Come on, Clarence. This will help.”

Castiel took a drink, hoping the caffeine would do its magic as soon as possible. “How’s your sweetheart?” Meg asked without looking up from the magazine she was reading.

Castiel turned his head to the right, stretching his neck until a satisfying pop was heard. “Fine. Sam’s leaving in a couple of days, so they are having dinner over at his uncle Bobby’s house.”

Meg flashed him a devilish grin, all teeth and smugness. “I didn’t mean your fake sweetheart.”

She meant Michael, of course. Castiel had just been a little confused because he was tired and needed sleep. “Horrible,” he answered honestly. “Haven’t talked much since our disaster non-date.”

Leafing through the pages, Meg stopped at a familiar article that Castiel could recognise even upside down, its title written in large pink letters.

“Which step are you on?”

“I don’t know, three, four?” Honestly, Castiel was in no mood to talk about Michael or the Cosmo-tips that had proven to be disastrous. He had half a mind to just give up already, Michael was not worth all the trouble. Then the image of familiar green eyes smiling affectionately at a short blonde appeared in his mind, and the coffee was suddenly too bitter.

Meg tapped her finger against the glossy page, seemingly unaware of Castiel’s sour mood. “The failed date. Next step is flirting, but we are skipping that because you’re hopeless.” She looked at him, her eyebrow raised as if challenging him to contradict her before she continued. “So now we have: Make him do things for you.”

Castiel swallowed down all complaints he had – he didn’t need to prove to Meg he knew how to flirt, the people that mattered already knew that – and instead tilted his head at her. “I don’t know what that means.”

Meg tutted, crossing her legs at the knee and reaching over to touch Castiel’s hand sympathetically. “What would you do without me as your wingwoman?”

“Why would Michael want to do things for me?” Castiel said defensively. “Why would _I_ want him to do things for me?”

“Clarence, do you really think women can’t open jars by themselves?”

“What does that-”

“Shush.” Meg brought a finger over his lips as she moved to sit at the arm of his chair. “No, we can use hot water, but we ask men because we want to flatter them and make them think they are the strong providers.”

“I don’t get it.”

“You don’t have to get it.” She waved a hand, rolling her eyes at him. “You only have to use it to your advantage. This is science, Clarence. Don’t question science. Men like to feel like strong providers.”

That was so sexist Castiel didn’t even know what to say. He didn’t feel any need to be a strong provider, and he definitely did not need one. “I’m not going to ask Michael to open a jar of pickles for me.”

“Of course you’re not. But you can ask him for help with the case.”

“I’m not doing that,” Castiel protested, shooting up and almost tripping Meg over in the process. “What will Chuck think?”

Flipping the hair away from her face, Meg glared at him. “Chuck spends more time watching failed proposal videos on Youtube than paying attention to his employees.”

“How do you know that?”

“I send them to him,” Meg said like it was the most natural thing in the world and Castiel was a dumbass for not knowing it. “Just trust me on this, Clarence. We need an extra pair of hands anyway.”

Castiel pondered her words for a moment. Then he shook his head. “Let's just finish this so we can finally get some sleep.”

***

The scent of freshly brewed coffee did nothing to ease the pounding of his head. Castiel glared at the coffee machine, urging it to go faster so he could just go back to his office and hide away the rest of the day while he rubbed circles at his temples with his fingers in a hopeless effort to soothe his headache. His co-workers buzzed around him, heels clicking on the floor, cabinet doors banging, voices too loud for what he could handle at that moment.

Why had he ever considered even for a single second that Meg’s suggestion was a good idea? Why? Why did he insist to torment himself? Even Meg had looked surprised when he had told her he had asked Michael for help.

A terrible idea. Disastrous even.

He should have seen this coming by the triumphant look on Michael’s face when he had spotted Castiel that morning to begin with. Michael had –as he himself had said – been more than happy to help Castiel, as soon as possible, too. Which apparently meant talking over Castiel, disregarding everything he and Meg had prepared up until that point and somehow ending up with: ‘ _Maybe I should take this over, Cassie, it’s a pretty big case.’_

_Cassie._

Castiel had been furious. Michael had spent the last five years barely acknowledging his existence – Castiel could admit that now – and somehow, he now acted like they were best buddies and all would be solved if he used the same nicknames as Gabriel and winked in a cute way. Which, no, Castiel had not found it cute. Irritating maybe.

This was his case. The client had come to _him,_ and _he_ had spent all those hours with Meg over papers and papers and papers. God, he needed coffee and two aspirins. He thumbed the phone in his pocket. Was it too early to send Dean a message whining about his lousy day?

Chuck dragged his feet into the kitchen, looking every bit as exhausted and bleary-eyed as Castiel felt. That was not new for Chuck, who, according to Inias, suffered from insomnia and could be found in the office until the wee hours of the night. Castiel had seen light in his office just last night while he was leaving with Meg.

Chuck came to stand beside Castiel, tie tied backwards and an empty cup with the photo of a puppy printed on it in hand. He stared at the coffee machine for a couple of seconds and then, as if snapping out of a daydream as soon as he realized that there would be more coffee soon, he turned to Castiel.

“Castiel,” he said surprised, like he hadn’t seen him standing right there all this time.

“Good morning, Chuck,” Castiel grumbled, hoping Chuck, too, was too tired for small talk. Unfortunately for him, that was not the case.

“Gabriel told me about your new case. Gallagher vs Adler.”

“It’s a difficult one,” Castiel said, choosing his words carefully. Complaining to your boss was never a smart idea, even if said boss was as ‘cool’ and ‘relaxed’ as Chuck – his words not Castiel’s.

Chuck hummed in agreement, his eyes back on the coffee machine. “Difficult but important. You know, Castiel, your hard work hasn’t gone unnoticed.”

Castiel turned to him with wide eyes. That was the last thing he expected to hear from Chuck today. “Thank you?”

“Yes, of course. You are one of our best,” Chuck continued, nodding more to himself than to Castiel. Then in a gesture that was decidedly Gabriel and not Chuck, he clapped him in the shoulder and squeezed. “I think you have very good chances of making partner if you win this.”

“I do?”

“Of course. You're a strong candidate.”

The coffee-machine beeped twice, signalling that the coffee was ready. Chuck sighed relieved as he poured himself another cup, completely missing how Castiel practically ran away from the kitchen, coffee forgotten.

Chuck thought that Castiel was a strong candidate for partner. He already knew that Gabriel was supporting him, but Chuck had always been more objective in his assessment of his employees and not moved by personal relationships and feelings. Castiel had spent the last few months convincing everyone – including himself – that he didn’t want that promotion, but now it was hanging so tantalizingly in front of him. Michael would be furious if he knew. Meg had heard him talking with Uriel, and Michael had said that he was practically partner already. God, Castiel had no interest in antagonising Michael.

Without thinking about it, Castiel found himself walking to the bathroom and hiding inside a stall, phone pressed to his ear before the door had closed behind him.

“ _Morning, sunshine.”_ Dean’s cheerful voice was like a lighthouse in the middle of a storm when he picked up his phone, barely two rings later.

“ChucksaidIamupforpartner,” Castiel blurted out, the words coming out of him mouth twisted and tangled all together, to the point even he wasn’t sure what he had just said.

A pause from the other end of the line and then, “ _Say that again?”_

Taking a deep breath, Castiel explained everything Chuck had just told him, this time speaking slow and clearly, his heart beating fast inside his chest.

“ _Wow,”_ Dean whistled, and Castiel could hear him moving somewhere quieter to speak to him, background noise fading completely with the sound of a door closing. Was he outside? “ _Cas, that’s amazing!”_

“Is it?”

“ _Of course,”_ Dean laughed, and the sound of it stirred something warm and golden inside Castiel. “ _Isn’t that what all you big lawyers want? ‘s what Sammy keeps telling me.”_

“But I-” Castiel started protesting, but Dean interrupted him almost immediately.

“ _Nuh-uh. No buts. You are the best lawyer I know, Castiel_ _Novak – well second best, gotta_ _support Sammy you know,”_ Dean said losing his thread of thought for a second and making Castiel chuckle in the process, “- _and you deserve this. You deserve this and so much more.”_

Castiel bit his lower lip, worrying it between his teeth for a second as Dean’s words sank in. This was a big opportunity for him, it really was. Slowly but surely, Dean’s enthusiasm rubbed off on him. These were good news, indeed. “Are you sure?”

“ _One hundred percent,”_ Dean answered without missing a beat. “ _Cas, trust me. You’ve got this. You’re going to win this beast of a case, and you’re going to get yourself a big fat bonus for it.”_

Michael didn’t seem to believe this, but Castiel was not going to bring this name up and ruin this moment. Dean was right. He could do this.

“Thank you, Dean.”

“ _Hey, anytime. Oh, gotta_ _go, I’m helping Jo with a few errands.”_ Long blonde hair flashed in Castiel’s memory, and a pit appeared in his stomach before he could stop it. Dean went on, unaware of the sudden coldness that had hit Castiel. “ _Hey, I meant to call to ask you, by the way, Sam’s leaving tomorrow and we were thinking of going for dinner. I know you are super busy, but you are invited. Sam said he really wanted to thank you for your help.”_

“Sure,” Castiel said feeling breathless. “Text me the details.”

“ _Awesome! That way you can tell him how much better_ our _lunch was. See you later, buddy!”_

The line went dead and Castiel was left alone in a bathroom stall, looking down at his phone. Their lunch had really been ‘awesome’ as Dean liked to put it. Dean had picked Castiel up from his office and driven them to a small bistro about ten minutes away. It was tucked away in a corner across from a park, with green wooden tables outside and mismatched chairs, with barely enough space inside to fit four high tables and their stools. Castiel would have never noticed it if Dean hadn’t pointed it out. The pasta though had been delicious. It was the best pasta Castiel had ever tried, handmade – as the owner and only chef of the bistro had informed them while they had been going over the menu – served in the pan it had been cooked in and topped with a generous amount of freshly shredded mozzarella that complimented the shrimp and white sauce perfectly. On second thought, delicious was not the proper word to describe it. More like divine. It had lived up to the owners claim and beyond, and the wine they had drunk with it had left them both relaxed and warm. Dean had been in high spirits that day. Sam’s visit had done him good. He'd been charming and funny and, if Castiel wasn’t delusional, just on the edge of flirty. Dean had even tried speaking a little Italian when their server had joked that if they'd loved the food so much, they ought to move to Italy. He'd spoken with terrible accent and butchered words of course, but Castiel had laughed so much his sides had hurt.

Castiel’s thoughts went back to the night he had first seen Jo and Dean working side by side. They had seemed comfortable around each other and definitely close. Very close. Closer than just work friends. But was there anything romantic between them? Dean spoke plenty about his brother and his uncle and even a couple of his friends – photos from his LARPing and Comic-con adventures with Charlie were still saved on Castiel’s phone – but Jo was... uncharted territory. Sam had said she was Ellen’s daughter, who was a family friend, so at the very least, she, Sam and Dean had grown up together. Maybe.

How was it possible that Castiel was spending so many hours with Dean or talking to Dean and there were still so many important things he didn’t know about him. Then again, if Jo was something like a romantic interest, Dean would have mentioned something. He'd been pretty open with Castiel from the beginning of their friendship. Unless Jo was an ex. Then Dean might not want to talk about her. He had to ask Dean discreetly at some point.

The bathroom door opened and closed, and somebody walked into the stall to Castiel’s right. Why was he in a stall thinking about one of the Roadhouse waitresses and her potential relationship to Dean anyway?

Oh right! Big case, promotion, Michael.

Castiel groaned, pocketing his phone. Fucking Michael. Castiel exited the stall and pretended to wash his hands, all the time thinking that he had to kick Michael out of the case while it was still early. There was no way he was giving second chair to him, let alone first, as Michael had been basically telling him all morning. These kinds of weeds had to be cut before they had time to grow deep roots.

The decision was easier said than done. Meg, who was filling her nails sitting at her desk, raised her eyebrows at him as he passed her in a warning that only became clear when Castiel entered his office. Michael was waiting for Castiel there, actually sitting in Castiel's chair, behind Castiel's desk like he owned the place, and playing with a stress ball – not Castiel’s.

“So, I’ve been thinking-” Michael started at the same time Castiel asked, admittedly more irritated than he wanted to come across as, “What are you doing here?”

Michael caught the ball he had been throwing in the air and stared at Castiel. Then a crooked smirk. “I’m here because you asked for help. Remember?”

Right. Not Castiel’s brightest moment. Or Meg’s. “Can I get back to you on that? I am kind of drowning in work.”

Michael’s face darkened for a split second, but then he got up and dusted off his suit. “Right. I’ll get out of your hair then.” He walked to the door but before he left, he turned around one last time. “How about dinner later? It might help you see things... clearer.”

Castiel, with his back to Michael as he rearranged papers on his desk, said, “Sorry, I already have plans with Dean.”

He didn’t turn around, but he heard the door clicking shut, and he exhaled, relieved. Maybe Michael had gotten the hint and wouldn’t come sniffing around Castiel’s case anymore.

A soft knock at the door and Meg let herself in, thankfully closing it behind her. “Trouble in paradise?”

“What paradise?” Castiel scoffed, shaking his head at her.

“With McDreamy,” she said, and then, noticing the blanc face Castiel gave her, she sighed. “Never mind, I forgot you’ve never seen Grace Anatomy.”

“Meg, I have so much stuff to do, if you are not going to help me, then please go back to painting your nails,” Castiel said, a little more aggressively than he had intended. He took a few folders from the many scattered all around his office and dropped them on his desk for emphasis. He was tired and exhausted, and he was really not in the mood to talk about his love life. He just wanted to finish his work and get out of there.

Meg searched his eyes uncertainly ,and Castiel stood there, never breaking eye contact. For the first time since they had met, Castiel thought that he'd finally cracked her cold and sassy persona. “Fine.”

For the next couple of hours, Castiel and Meg worked in silence until they managed to go through the last folder. A small path of bread crumbs had started forming in Castiel’s mind. He only had to follow it and find the connection that would finally win him the case. But not that day, because his brain was at the edge of crawling out of his ears and committing suicide.

He checked the time and even though it was a little early, Castiel figured he deserved some rest. He stood up, walking towards the hook behind the door where his trench coat was hanging.

“Where are you going?” Meg asked, watching him curiously as she organized all the papers and documents.

“I have to go,” Castiel said, putting on his coat and nodding goodnight at her.

“Castiel,” Meg said, and the lack of sarcasm in her voice made him stop. “If he is the one, it should come naturally to you.”

Great, more advice. Castiel waved a hand over his shoulder. “I’ll see you tomorrow.”

He arrived at the restaurant earlier than they had agreed, but once more Dean had beaten him to it. He and Sam were already sitting, each of them with a beer in front of them, munching on breadsticks. They were sitting close to each other, heads ducked close, and Castiel could tell from the way Dean’s mouth was pressed in a thin line and Sam’s brow creased in the middle that they were arguing about something. Dean’s face lit up when he spotted him, and he eagerly waved him over, his previous conversation with Sam cut short at a ‘ _-just looking out for you, Dean,’_ and ‘ _Shut up, Sammy.’_ What they had been arguing about, Castiel could only guess at ,but he really hoped that it had nothing to do with his own conversation with Sam a few days ago at lunch.

Castiel was dead tired and it showed, so they made an effort to keep a light topic throughout their dinner. Sam had finally told Dean about the move and was already looking for a house, even though both Dean and their uncle Bobby had insisted they had a spare room for him and his fiancé if they hadn’t found anything they liked by the time they moved out here. Dean talked wishfully about his plans with Charlie and Ash – a man Castiel vaguely knew by name as working at the Roadhouse the nights Dean had off - to go to the movies over the weekend. Castiel was invited, but he refused, saying he wanted to get as much sleep in as he could. The Gallagher vs Adler case was taking too much out of him, and the preliminary hearing was almost around the corner.

Sam smiled sympathetically at him from across the table. “I know the feeling.”

“I’m just sorry we didn’t have the opportunity to hang out more while you were here,” Castiel said.

Laughing, Sam brought his beer to his lips and took a sip. “Don’t worry about it. I’ll visit again soon with Eileen. That way you’ll meet her as well.”

“I’m sure she's an amazing woman.” Castiel didn’t say that just to flatter Sam - he truly believed it from what he had heard from both Sam and Dean - but Sam flashed him a bright smile anyway.

“She is too good for you, Sasquatch.” Dean circled his spoon with a bite of steak stuck to it at his brother. “Watch as she becomes big and famous and you are left at home taking care of the little ones.”

“I hope she does,” Sam grinned, glowing with pride.

Eileen, Castiel knew, was a journalist who was also writing her first novel, a crime story about a man whose sister went missing without leaving any trace behind. Castiel was looking forward to reading it once it got published, and even though Dean had joked he’d wait for the movie, he’d told Castiel in private that he’d already read some parts Eileen had emailed him, and he was hooked.

Plates cleared and beer bottles emptied, Dean leaned back in his chair, a hand over his stomach. “Look at that. It’s a food baby. Cas, you’d better take responsibility for this.”

“Why me?” Castiel asked, acting scandalised but biting back a smile.

“Because it’d be weird if my brother took responsibility for my baby.” The _duh_ was left unsaid, but was very heavily implied. Dean wiggled his eyebrows. “If you like it then you shoulda put a ring on it.”

Sam chuckled, throwing a paper napkin at his brother, who easily caught it in mid-air with a smug look on his face. “I’ll take responsibility,” Sam said, getting up. “Or at least I’ll get the bill.”

“No, Sam, I insist-”

Castiel started getting up himself but Sam waved him off.

“Don’t even think about it, Cas. This one’s on me.”

“Thank you very much then.”

“Yeah, thanks, Sammy,” Dean grinned up at his brother. “Don’t forget my to-go dessert.”

Sam rolled his eyes as he wandered away to find their waiter and settle their bill.

Dean watched him go, chewing the inside of his lip. “Hey, Cas,” he said. “Thank you for helping Sammy. He told me you gave him the phone of one of your lawyer friends.”

“Dean, it was my pleasure. Sam is a very smart young man, and he has a bright career ahead of him.”

Dean flushed with pride at that. “That’s my Sammy, the career boy.”

“It looks like a good time for you to start thinking about your own career options,” Castiel said, remembering all the things they had talked about at the diner on their first ‘date’. “You could look into that cooking school you were talking about.”

Dean frowned, thinking over Castiel’s words before replying. “I don’t know.”

Castiel could easily tell that Dean was uncomfortable with this topic, so he decided to give him an easy way out. “Are you scared you’re gonna suck?”

Dean glared at him. “I’ll have you know that I’m an excellent cook.”

“So you keep saying, and yet you still haven’t cooked for me.”

And there it was. Dean Winchester’s irresistible, crooked smile, followed by his signature wink. “I’m just looking out for you. If you try my cooking you might fall in love with me, and then there goes our Cosmo-plan.”

Castiel paled at the reminder of their Cosmo-plan, and his stomach dropped, at the same time it filled with butterflies, because here was Dean talking so easily about them falling in love but so quickly dismissing it. Dean, who had just seen Sam coming back, didn’t notice a thing.


	7. Step 7: Try alcohol to loosen up

The pressure was on. The preliminary hearing had been a success, and now they had a date for the trial - sooner than Castiel would have liked, but he could still make it. Castiel and Meg had spent the whole week preparing and digging up information on their witnesses. To say they were running solely on coffee and carbs would be an understatement. With their lunch break approaching, Meg stretched her arms over her head, more than ready to get out of the office and stretch her legs as well. “God, sometimes I think it’s better the trial is early. I don’t think I could do this for much longer.”

“If the trial wasn’t so early, we wouldn’t have to work such long hours,” Castiel pointed out, his eyes trained on the list of questions he was going to ask Adler. His back was hurting from so many hours hunched over his desk, and Meg didn’t look any better. He had to start thinking about that couch more seriously. It would have been nice to have somewhere to wind down, even if for just a few minutes.

A knock at the door made them both turn towards it as it opened to reveal Michael. “You guys look awful,” he said, shaking his head at them. Turning his attention to Castiel, he quirked an eyebrow. “Do you need any help?”

“No, thank you,” Castiel answered coolly. “Everything is under control. Now excuse us, but we really need to focus.”

The only indication that Michael had been bothered by Castiel effectively giving him the cold shoulder was a minimal tightness to his jaw, but he left without any other comment. Thank God.

“Congratulations, Clarence,” Meg said, reaching over the desk and offering her hand for Castiel to shake. “You finally see that Michael is a self-absorbed dickhead.”

Castiel took her hand and shook it firmly. He and Michael were not exactly in any kind of race, but this still felt like a mini victory. “I’m seeing a lot of things more clearly lately.”

Meg tipped her head to the side, leaning forward to rest on the desk with her elbows, fingers laced together. “Like what.”

“Like the fact that you deserve that parking spot-” he pointed a finger at her, “-and I’m going to win it for you. For both of us.”

“Sooo,” Meg dragged out her word in that way she did when she feigned innocence but was really preparing to go in for the kill, “you don’t care if Michael sees you as competition anymore?”

“He already does,” Castiel shrugged. “I might as well have a bigger office so he has an actual reason to.”

“Clarence, colour me impressed.” Meg clapped her hands together delighted. “Where did that change of heart come from?”

“I've been thinking about this a lot lately.”

“I could take a guess about when you started.”

“I’d be worried you’re losing your edge if you couldn’t.” Castiel raised his eyebrows at her, earning an annoyed huff from her, but he knew Meg well enough to know she was just faking annoyance.

She pushed herself up from the armchair and threw the papers she was holding in front of Castiel. “Okay, that’s sappy enough for today. I-”

_Knock knock_ _knock_

Meg and Castiel eyed each other curiously. “You sure are popular today,” Meg said at the same time Castiel craned his neck to look at the door behind her and said, “Come in!”

The door opened enough for Gabriel to stick his head in and wink at both of them. “How are my two best friends doing today?”

“I don’t know, haven’t seen them,” Meg answered without missing a beat. Glaring at her only made her smile wider, and Castiel settled for rolling his eyes.

“Megan! Always the funny one.” Laughing, Gabriel stepped inside the office. He walked to Meg and pushed both his hands on her shoulders giving them a squeeze. “Just remember who’s paying both of you.”

He tilted his head at her, a smirk playing at the edge of his lips. Meg, to Castiel’s surprise, mimicked zipping her mouth.

“Gabe,” Castiel said instead of a greeting, standing up too.

“Chuck and I are going to dinner tonight. We want you to come with us. To discuss a few things.”

“A few things?” That sounded ominous to Castiel but judging from Meg’s face, who was grimacing at him as subtly as possible, ‘ _yes_ ’ was the only correct answer.

“Only good things,” Gabriel reassured him. “It’s a pretty big case you are handling after all.”

Castiel cleared his throat, giving Gabriel as much of a confident smile as he could master. “Oh. Then I’d loved to.”

“Wonderful. Dean is invited too, of course,” Gabriel said, walking backwards towards the door. “I know it’s a little last minute but I don’t want Kali to feel lonely. I’ll email you the details.”

“I’m sure he’ll try and make it.”

The door had barely closed behind Gabriel before Meg appeared next to Castiel, both of her hands on his face. “This is it, Clarence.”

“Excuse me?” Castiel tried to say, but it came out muffled with the way Meg was squeezing his cheeks between her palms.

Meg’s eyes shined with renewed exuberance, and her nose was almost touching Castiel’s as she whispered, “You are top candidate for partner.” Then she released him and spinning around, almost dancing, she threw her arms over her head. “My hard work is finally paying off.”

“ _Our_ hard work.” Castiel touched his jaw that felt a little stiff from the way Meg had been squeezing him a few minutes ago. He moved it from side to side, opened and closed his mouth. A little crack was heard. No pain though, so that was bound to be a good sign.

“Whatever, Clarence. You’d be lost without me,” Meg said, throwing him a wink over her shoulder. “I’ll get us coffee and some snacks. Lemon muffin, right?”

“Actually,” Castiel said, and Meg grinned like she knew what he was about to say, “I’m gonna go for pie today.”

“You got it, boss!”

The staccato of her heels faded as she strode away.

Castiel sent Dean a quick message asking him about dinner, saying it would be fine if he couldn’t make it although Castiel really, really, _really,_ wanted him there for support. That last part of course wasn’t in the text.

Instead of texting back, Dean called Castiel five minutes later. “ _Should I congratulate you?”_

“It’s just dinner,” Castiel answered, but he was secretly pleased with how fond Dean sounded over the phone.

“ _Dinner with both your bosses? That sounds like a big deal to me.”_

“I don’t like to brag...” Castiel broke his sentence off, playing coy, and Dean barked a laugh on the other end.

“ _Jeez, Cas. That’s huge news.”_

“Will you be there?”

“ _Obviously!”_ Dean declared. “ _Gotta_ _support my boyfriend, right?”_

Castiel’s heart missed a beat at the sound of the word ‘boyfriend’. “What about your work?”

“ _Don’t worry, I got Jo and Ash to cover for me.”_

Dean had to reassure Castiel three more times that it really wasn’t a problem and no, Ellen didn’t mind if Dean missed a day since he'd found someone to cover for him. In his own words, ‘Cas needed to chill.’ They hung up, Castiel promising to call Dean again for more details, and it was only then that Castiel realised, that finally, _fucking finally_ , things were going his way. His career was in a great place, he was mentally better than he had been in the last few months, and he was cutting toxic people out. And as for his love life, well, hopefully his love life would get a boost soon too. Castiel didn’t want to jinx it by being too optimistic. He still had to make sure Dean was not interested in anyone else. Somebody blonde. Who had just agreed to cover for Dean so he could go out for dinner with Castiel.

Castiel shook his head. He was not going down that rabbit hole of paranoia and assumptions. He would just ask Dean face to face, like adults do. Or he would try and get it out of him discreetly. Maybe the second option was better.

***

At Meg’s insistence, Castiel left work early to go home and prepare for dinner that night.

‘ _Win us that promotion and I’ll win us the case._ ’

Castiel felt a little guilty for leaving her to deal with the bottomless pit of work they still had to do, but he trusted her. If anyone could pull through, it was Meg.

He was getting out of the shower, water still clinging to the ends of his hair and a fuzzy towel wrapped around his middle, when he noticed the notification for a new message on his phone.

Dean had sent two pictures, taken in front of his mirror, in two different outfits. The first one was a black pair of pants with a slim blazer and a dark blue shirt underneath. The second one was a pair of dark grey pants - tighter than the first Castiel noticed – with a light grey shirt, sleeves rolled to his elbows, and a charcoal waistcoat on top. He looked amazing in both pictures, and Castiel’s eyes trailed the hard lines of muscle that were barely visible underneath the clothes. Shit, he had to take his mind out of the gutter or he would need a second shower.

‘ _A or B??’_ Dean had written underneath the two pictures.

It was not an easy choice, but Castiel had to pick B, for reasons completely unrelated to how he imagined Dean’s ass would look in a tighter pair of pants, or to Castiel’s own fetish for sleeves rolled to the elbows. Yes, Castiel was being completely objective here. Black was a boring colour anyway.

An emoji with sunglasses arrived shortly after as an answer, followed by a second message, asking where Castiel wanted to meet.

_< < To: Dean W. 17:13_

_Pick me up around seven?_

_> > From: Dean W. 17:16_

_If you wanted a ride in my Baby you couldve_ _just asked_ 😉

Castiel rolled his eyes, but he texted Dean his address, waiting only long enough to see a ‘thumbs up’ emoji appear at the bottom of their conversation, and then he opened his closet with a more pressing matter taking up all his attention. What was _he_ going to wear?

***

Castiel slid in the passenger seat of the Impala, smoothing down the front of his shirt. He'd chosen one of the suits he had picked with Dean and paired it with the tie Dean had said brought out his eyes. His room looked like it'd been hit by a tornado after he'd tried on almost every single article of clothing he owned until he chose this, but seeing Dean’s bright green eyes fall to inspect Castiel from head to toe and then back up again, with a slight pause that Castiel may or may not have imagined at his hips and his lips before meeting Castiel’s eyes again, made it all worth it.

“Looking good, Cas,” Dean whistled appreciatively. “Everybody at the restaurant is gonna be jealous of me.”

Castiel eyed Dean, noticing that he had worn the outfit Castiel had chosen, and that, yes, it really did hug him in all the right places. “And here I thought that they’d be jealous of me for my handsome date.”

Dean’s cheeks flushed bright red, but he laughed good-naturedly.

The ride from Castiel’s apartment to the restaurant was about twenty minutes, and Castiel was content to sit back, music blasting as Dean shook his head to the rhythm, mouthing the words without actually singing. Castiel thought he was adorable, but he didn’t say so. Instead he kept stealing glances at him, biting down his fond smile.

“You look excited for tonight,” Dean noted, fingers drumming on the wheel.

“I am,” Castiel admitted. “Thank you for coming with me tonight, I need the support.”

“Don’t mention it. I'm sure you would’ve killed it on your own, too, though,” Dean said.

Thumbing the leather of the seat next to his thigh, Castiel chose his next words carefully, trying to make his voice sound nonchalant and casual. “I guess I owe Jo one for covering for you.”

“Nah, she didn’t mind,” Dean, said stealing a glance at Castiel. Then, as if the thought had just occurred to him, he added, “Plus, she owes me for all the times I told Ellen she was hanging with me when in truth she was sneaking out to meet with her boyfriend in high school.”

Castiel frowned. “High school was a long time ago.”

"Sure, but the trauma of Ellen finding out and grounding both our asses for two months still keeps me up some nights,” Dean joked, his eyes getting that faraway look Castiel was so used to seeing when Dean told him a story about when he and Sam were children.

“She found out?”

“Of course she did. I swear Ellen is better than the FBI. Jesus, I was scared shitless. You should have seen my dad’s face when she called to announce I’d spend the summer washing dishes at the Roadhouse. To this day I don’t know what she told him exactly, but I swear to God, he went pale as soon as he picked up the phone.” Dean physically shivered at the memory. “Jo will owe me forever.”

“You two are close then,” Castiel said, hearing a hint of jealousy leaking through his words.

Dean squinted at him confused. Then he turned a shit-eating grin on Castiel, easily seeing through Castiel’s bluff. “Jesus, Cas. She’s like my little sister.”

“I’m just asking.”

“And I’m just answering,” Dean said, but the grin that stayed stuck to his face until they reached the restaurant clearly showed he was pleased Castiel was jealous. At least Castiel could count this as a point in his favour.

They were the first to arrive at the restaurant, but Gabriel and Kali found them while they were still waiting to be showed to the table Gabriel had reserved. By the time they'd been seated and ordered their drinks, Chuck showed up too, and soon they were studying the menu. There were plenty of dishes that looked delicious, and if it wasn’t for the server’s help pointing out the chef’s specialties and their most popular dishes, they could have spent a whole hour just deciding what to order.

The atmosphere was light and relaxed. Nobody was in the mood to talk serious business after a long day at work and on an empty stomach, so they stayed on more light-hearted topics. Dean’s humour shined, easily winning over Kali, who kept him on his toes with her sharp tongue and quick wits but enjoyed herself immensely and laughed louder than everyone else.

Castiel didn’t want to jinx it, but things were going well. As a matter of fact, they were going too well, and so, of course, something had to happen and ruin his day.

At first, Castiel thought he’d had imagined it, catching a glance of a familiar figure talking to a waiter at the door, but then, just a few minutes later, that familiar figure reappeared, and this time there was no mistaking who it was or where he was headed.

Michael was strutting towards their table.

“What a coincidence,” Michael said, stopping at their table at the same time Gabriel and Chuck exchanged a confused look.

Now, Castiel didn’t like to be suspicious of people and generally he left the ‘thinking the worst about someone’ to Meg, but this was so painfully obviously not a coincidence he wanted to laugh. Michael showing up in the same restaurant as them, almost at the same time and, surprise, surprise, alone. Yes, what a big, funny, coincidence.

There was an awkward moment that Michael was standing above their table, Kali and Dean staring at him, Castiel looking from Gabriel to Chuck, who seemed like they had a silent discussion with their eyes. Then Chuck waved a waiter over and asked for one more chair. Why not join them since he was already here, anyway?

And that was how Castiel found himself sitting next to Michael and having to move his chair just a millimeter to the right because Michael was taking up so much space with his feet spread wide under the table and his hands resting on the table so far from his body one of them was practically on Castiel’s empty plate.

Castiel took a deep breath, forcing his muscles to relax and pressing his hand flat on the table to keep it from closing into a fist. To his right, Dean brought his own hand up, right next to Castiel’s, their pinky fingers brushing against each other. Castiel turned to look at him and saw the question in his eyes. A _re you okay?_

He nodded briefly, silently thanking him for the support.

“I didn’t mean to impose,” Michael said after he'd given his order, cocking his head to the side to glance at Castiel. He turned to the rest of the table, flashing them a wolfish grin that a couple of months ago would have Castiel swooning after him, but was currently only causing his blood pressure to rise, and not in a nice way. “Kali, you look beautiful as always.”

“And you, a flatterer as always,” Kali answered gracefully, taking a sip of her Chardonnay.

“So, like I was saying before,” Dean jumped in easily catching Gabriel’s attention again, “if you want to know where to find the best chocolate cake, I can tell you, but it will cost you.” He wiggled his eyebrows suggestively.

Gabriel leaned forward. “You got my attention, Winchester.”

Dean grinned, brushing his finger against Castiel’s once more reassuringly, before he and Gabriel started bargaining for a price,‘ _You_ _are telling me you won’t trade it for the best chocolate cake_ and _their secret recipe?’ ‘I can’t tell you where I buy the donuts from because if they become famous then I’ll never find my favourite_ _flavours_ _anymore.’_

Rolling her eyes at her husband's antics, Kali focused on Castiel. “I hear you have a big trial coming, up,” she said. “Something involving a pharmaceutical company?”

“It’s a pretty big case,” Chuck added. “I’d love to hear how you are going with it.”

“We’re working on it,” Castiel answered and then opened his mouth to continue but was cut off by Michael.

“Well, actually-”

Michael started talking endlessly about statistics and similar cases, acting as if he was the one in charge of the case instead of Castiel. Which was ridiculous. Michael had barely had time to look at the case before Castiel had asked him to step back and let him handle it on his own. And he wouldn’t even know anything about it in the first place if Castiel hadn’t been stupid enough to ask for his opinion.

Which was a shitty opinion, by the way.

The waiter chose that moment to appear with their food, saving Kali from Michael’s endless monologue. Taking advantage of everyone else’s attention being on the plates placed in front of them, Chuck leaned forward quickly and whispered to Castiel, “We are very impressed, Castiel.”

There was no stopping the smile that formed in his lips. Just as there was no stopping the sour expression on Michael’s face. If he'd eaten a lemon, he’d have handled it better. Instead of getting the hint and shutting the fuck up, Michael only became even more obnoxious from then on. Castiel could barely say a word before he jumped in to monopolise the conversation. Again.

It was halfway through their dinner that Castiel realised he hadn’t touched his food at all. How could he, when his stomach was in a tight knot and really, he’d much rather drink. How many glasses had he had? Four? Five? He’d lost count.

Distantly, he heard Michael excusing himself to answer his phone. Castiel ordered another drink, and it was only when Dean placed his hand on Castiel’s knee that he realised that he'd been tapping his foot nervously for some time.

“Are you okay?” Dean asked in a low voice, leaning close to Castiel.

“I’m fine.”

“Are you? You’ve had more wine than all of us combined.”

“I’m fine,” Castiel grumbled, louder than he intended. Gabriel and Chuck turned to him surprised. “Excuse me.”

He got up, ignoring Dean’s worried eyes on him and walked to the restroom. He splashed water on his face and then stared at his reflection in the mirror. He looked... well, not a mess but not exactly presentable either. The cold water had done nothing to revert the flush on his cheeks and even less to calm his nerves. Another movie cliché that proved to be bullshit.

Castiel could feel his nerves vibrating with anger, his blood boiling under his skin. He had to get out of there – the restaurant, not just the restroom – before he did something stupid like punching Michael in front of everyone and destroying his career once and for all. Gabriel could be tolerant on a lot of stuff, but Castiel was sure physical assault was not one of them. He took a deep breath, holding it in and counting down to five, and then exhaled. He had to get out of there.

He was in the middle of texting Dean to come with an excuse for both of them to leave ASAP, when fate decided it had just one more trick up its sleeve. Of all the people that could walk into the restroom at that precise moment, of course it was Michael who did.

Fucking hell. Castiel just couldn’t catch a break.

“Hiding in the bathroom Castiel?” Michael stood next to him, inspecting his hair in the mirror.

Castiel could be the bigger person here. He could keep his head high, and walk out, and explain everything to Gabriel later when he would have calmed down.

He could.

But he didn’t want to.

“What are you even doing here, Michael?”

“In the bathroom?”

“In this restaurant. Because don’t think I believed for even a minute that you just happened to decide to come eat here today. Alone.” Castiel was so tired of all these games.

Michael turned to face Castiel, his eyes narrowing, a small vein straining against his temple. “What, you think I’m going down without a fight?”

“A fight?” God, Michael was so full of shit. The wise choice would really be to just turn around a leave.

“You were never interested in the promotion before... before _him_.”

And here, finally, Michael was showing his true colours.

“Him? You think Dean is the reason I changed my mind?” Maybe it was time for Castiel to show his true colours as well. All cards open on the table. Maybe that would get Michael to shut up before he said something else about Dean like whatever he'd hinted at when they had dinner. Castiel couldn’t promise that he wouldn’t hit him this time if it came to that. “You knew I had romantic feelings for you, and you even encouraged it a few times when it suited your plans” - yes, Castiel could admit that now - “and all of that just because you didn’t want me pur-”

Michael cut him off with a kiss, silencing Castiel’s protests with his lips. It was aggressive and bruising, and it felt more like an attack than anything else. It was over before Castiel had time to react.

Castiel spit in the sink, rubbing the back of his palm over his lips. “What the fuck?”

Michael, who had been staring at a spot behind Castiel, turned to Castiel and smirked satisfied. “Thank you.”

“Just stay away from me,” Castiel warned, clenching his hands in fists to hide their trembling. “I want nothing to do with you.”

Still with that satisfied smirk on his face that was just begging Castiel to wipe it off his face and break a few of his teeth in the process, Michael shrugged. “I don’t really care.”

Castiel did not run away from the restroom. He strategically retreated. He'd had such high hopes for today. And fucking Michael had to come and ruin everything. That asshole. That-

Castiel’s thoughts – and footsteps – came to a halt as soon as he saw their table. Or more specifically, the empty chair where Dean should have been sitting in.

“Where’s Dean?” he asked, a terrible feeling in his gut.

Chuck frowned at him confused. “He came to find you and then returned looking upset. He said he had to leave.”

Fuck.

“Did you two fight?” Gabriel asked concerned.

Fuck. Fuck, fuck, fuck.

If Castiel was in a movie, this was the moment where a flashback would be shown. As it was, the flashback played only in his eyes, from his fight with Michael, to maybe the sound of a door opening while Michael kissed him, to the way Michael had been staring behind Castiel afterwards. Staring at the door.

_Fucking fuck._


	8. Step 8: Confess your feelings

Friday dawned like every other day before it. The sun was brighter than it should for the time of the year, and despite the slight chill hanging in the air, most people still felt like summer was just a few days ago.

Except Castiel.

He'd spent one more night sleepless and stressed. His phone lay flat on his nightstand, dark and silent. Castiel had checked it at least three dozen times while he waited for the sleep that eluded him. He'd called Dean five times, all unanswered, and had sent a dozen texts that were probably never read. He got up and dragged his tired body to the shower, hoping the cold water would rejuvenate him.

It didn’t.

He sent another text with just four words: _Please talk to me_.

No answer came back.

No surprise there really. Castiel didn’t know why he expected Dean to magically change his mind and talk to him.

He poured himself a cup of coffee to go with his poor excuse of breakfast – toasted bread and a tangerine – and drank it in two gulps. He poured himself another one.

This was not how his Friday should have gone. Correction. It was not how his Thursday evening should have gone. If Michael hadn’t shown up uninvited to that dinner, and if he wasn’t an asshole, and if Dean hadn’t come to the bathroom...

Castiel knew how he had expected the dinner to go for his career. But for Dean, things were a lot vaguer. He'd been hopeful that they could come closer. That things would just naturally progress in the direction he wanted them to. They'd already almost progressed to that direction twice before. If only shit could stop getting in their way.

Castiel sullenly made his way to his car, already mentally prepared for the longest day ever. His phone rang just as he was opening his door, but despite all of Castiel’s prayers and loud heartbeat, it was Meg. She cut to the chase almost immediately, telling him to stay away from the office and instead meet her at Starbucks. She hung up right after that leaving Castiel to stare at his phone in confusion. Soon after that he received a message with the address, asking him to ‘get his ass over here ASAP.’

Somehow that did not sound good to Castiel.

Apparently, the universe was not done destroying his life yet.

He found Meg in the back of the room, where she had claimed the largest table available for studying and working. Half of the other customers shot him a dirty look when he joined her, before hunching over their laptops on the lower tables available. Too bad for them Castiel was too tired to care.

Castiel threw his trench coat on one of the chairs as Meg pushed a cup of coffee towards him. “What happened?”

Meg glanced at him quickly and then went back to typing furiously on her laptop. “I didn’t think the firm was a good place for you to be right now.”

“Why not?”

Her fingers paused briefly above the keyboard, and then she continued her work, hitting the buttons with more force than what was good for them. “There are some rumors going around.”

Castiel’s stomach fell to his feet. This was definitely not good news. “What rumors?”

“About last night.”

“Oh.” Yeah, definitely bad news.

Meg turned to look at him dead in the eye. “Did you and Dean really break up?”

The question hit him like a bullet straight in the gut, and, judging from the way Meg’s face changed to a grimace of sympathy, he didn’t do a good job of hiding it. He rubbed a hand over his face. “It’s complicated.”

Mostly because Dean and Castiel were never dating so they couldn’t have broken up, but that didn’t seem to matter to Meg.

“Try me.”

With a sigh and the memories of last night weighing heavily on his shoulder, Castiel gave her the quick version of Michael showing up out of the blue and destroying, if not Castiel’s career, then definitely his chances with Dean. Meg slammed her fist on the table.

“That fucking asshole,” she roared, and everyone turned to look at them. “That motherfucker.”

“Meg, please! People are staring.”

Glaring. They were glaring. But Meg didn’t care.

“He’s such a dickhead!”

“Meg!”

“Shhhhh,” a girl with pink headphones reprimanded them with a finger in front of her lips. Meg narrowed her eyes at her, but she lowered her voice.

“It’s true. Did you at least catch up with Dean to explain?”

Castiel shook his head. “He’d already left when I ran to where we'd parked.”

“Did you-”

“Yes, I called. And texted him. And called again. And texted some more. He is not answering.”

“Of course he isn't,” Meg said exasperated. “God, I can’t believe Michael would go to such lengths just to throw you off balance and lose the case. He must be desperate.”

“I know.”

“We won't let him,” Meg assured him, setting her jaw. “Get back to work.”

Castiel did as commanded, but it was hard to concentrate. The letters were dancing before his eyes, and at one point he had to read the same sentence five times to understand what it said. His mind kept wandering to Dean and what he might be doing at that moment. His hand kept going back to his phone, lighting up the screen with a press of his finger only to be disappointed one more time when there was no answer to any of his texts.

Meg helped him go over their notes and check their strategy one more time, repeating the questions they'd prepared for the witnesses, and that forced him to focus, even for a few minutes. They went back and forth, doing their best to build a solid case, but it was not enough. The only thing Castiel had was a list of Adler’s patients that had received the treatment seemingly without any reason to – Gallagher included – but none of them had ended up in the hospital. He had another doctor that would testify against Adler and explain to the court why Gallagher didn't need that prescription in the first place, but he needed more. Adler could argue that it couldn’t be proven that Gallagher ended up in the hospital because of the treatment he had recommended, and he had plenty other patients that were just fine. Too many patients actually. There must have been something in it for Adler to involve so many of his patients in this, but no matter how many times he searched Adler’s financial records he couldn’t find a connection with Holy Hosts Pharmaceutical.

Or maybe he hadn’t looked in the right place yet. There must have been something. Anything. Even if it was just a paid trip. If Castiel could just get his shit together and stop checking his fucking phone he could find it.

His phone buzzed next to him and all thoughts about the court were thrown out of the window. He answered without even looking at the caller ID.

“Dean?”

“ _Gabriel, actually,”_ the answer came from down the line.

Fuck. Castiel had forgotten that Gabriel had witnessed the whole circus last night.

Fuck.

“ _Listen, buddy, I know you have a lot on your plate right now. I wanted to check in on you.”_ Gabriel spoke carefully, tip-toeing around the subject like he was afraid of stepping on glass.

“Everything’s fine, Gabriel. I promise.”

At the mention of their boss’ name, Meg scooted her chair closer, and Castiel angled his phone between them so that she would hear what was being said.

“ _Are you sure? Because I don’t see you here today.”_

“I- uh. Meg and I thought a change of scene might help us.”

Meg gave him a thumbs up, but Gabriel didn’t sound convinced. He hummed softly before answering. “ _It’s an important case. If you are not up to it, somebody else could-”_

“What? Gabriel you can’t give the case to anyone else.”

Meg agreed silently.

“The trial is on Tuesday, and it’s Friday now.”

“Nobody else has studied the case,” Meg added.

“ _Michael said he was helping you-”_

“That fucker!” Meg yelled into the phone and once again half the people lifted their heads trying to murder her with their eyes only.

A pause. “ _Cassie?”_

Castiel pushed Meg away, warning her to keep quiet and pressed the phone in his ear. “Just trust me, Gabriel. I've got this.”

He had to do this.

“ _Okay. But I need full transparency here. You email me everything you have and keep me updated.”_

“Done!”

“ _And-”_ Gabriel added, putting more emphasis on his next words, “- _you come by my office on Monday and show me all your arguments and evidence, and I have to approve of everything_ _before you walk into that court on Tuesday.”_

“Anything you want,” Castiel agreed and had to reassure Gabriel three more times that he really was giving his everything for this case. It wasn’t a total lie. Castiel was trying his hardest to concentrate.

“Fuck Michael,” Meg said hotly. “We are going to win that case, and then we are going to get you that hot piece of bartender ass.”

Castiel opened his mouth and closed it again.

Meg raised her eyebrow at him. “Jeez, Clarence. It’s so obvious you’re totally gone on this guy. And I bet you my new parking space he feels the same way.”

For lack of a better answer, Castiel just said, “It’s not yours yet.”

Meg waved him off. “It’s as good as mine. We’ll win this case even if I have to threaten the judge to do it.”

She pointed at the papers in front of them with her pen, ordering Castiel to get back to work. And he tried. He really did. But with the way his head was pounding, trying to feed on the caffeine running in his veins to stay awake, the only thing he could do was think in circles about... well about everything. And Dean. Mostly Dean, if he was being honest.

Meg had said that Dean liked him, and Castiel almost believed it. Almost. “Do you really think that?”

“Do I think what?” Meg asked absently, writing down some notes.

“That Dean feels the same way.”

“I have eyes, Clarence,” she answered without looking up. “And I’ve seen the way he looks at you.”

A blush crept up Castiel’s cheeks. “Isn’t that too sappy for you to say? Cliché?”

Considering his words for a moment, Meg bit the end of her pen. “Cliche isn’t a bad thing. And he got pretty upset about Michael. I think Dean-o is head over heels for you.”

Castiel pouted, ignoring the little voice in the back of his head telling him that he was acting like a five-year-old. “He isn't answering his phone. He's probably not even reading my texts.”

“He's hurt,” Meg offered. “Keep trying, and if he doesn’t answer by tonight, go and knock on his door until his neighbors force him to come out and talk to you so they can get some sleep.”

“Why do I feel you’ve tried it?”

“Love is a hurricane, Clarence.”

A beat and then, “I don’t know where he lives.”

Meg rolled her eyes at him. “You are hopeless. You guys have been plotting and fake dating for more than a month and you don’t know where he lives?”

“It’s not like I was stalking him.”

“But you do know where he works.”

Castiel blinked at her. “I can’t go there. It’s not right of me to ambush him where he can’t shoo me away and he can’t leave either.”

“Go early. Before his shift starts. You know when his shift starts, don’t you?”

Castiel nodded slowly. “What if he doesn’t want to talk to me?”

Meg pressed her lips together in a way that said, _God, help me. “_ He will, once he sees you.” Then she tapped her finger on the paper Castiel was supposed to be reading. The discussion was clearly over, and it was time to get back to work. Castiel ordered another coffee and dove headfirst in the papers. With a plan in mind it was easier to get into a rhythm, and they made good progress, but there was still that small piece of information missing. The connection.

They worked side by side until both their brains were fried, and even Meg had to admit that they needed a break. They gathered their papers and laptops and found a restaurant close by, where they shared mozzarella sticks and stuffed their faces with pizza. The huge, cheesy slices left his fingers feeling greasy and were definitely not a healthy choice, but they did make him feel slightly better. He decided giving Meg’s idea a go was worth a shot after all.

And that’s how he found himself parking his car in the back of the Roadhouse, in the same spot he'd seen Dean leaving his Impala a couple of times. Said Impala was nowhere to be seen though. That didn’t mean Dean wouldn’t show up at some point. Castiel knew his shift started around seven, and it was barely six now, so it was completely possible Dean hadn’t arrived yet.

Castiel knocked on the back door anyway.

He knocked once, twice and waited a couple of minutes without answer before knocking again a couple of times. Then, the door opened to reveal a mullet-wearing, gangly man that Castiel had seen working with Dean behind the bar on one of the busier nights at the Roadhouse. He assumed he was the bartender Dean referred to as ‘Ash’.

“’Sup man,” maybe-Ash said. “You the new accountant Ellen’s been waiting for?”

“I- uh... no. I’m here for Dean.” He shifted his weight from one foot to the other and then added, “Winchester.”

Maybe-Ash's eyes shone with something close to recognition as he scratched his chest over his crisp white shirt. “Dean-o’s not here right now.” He turned to look inside and then back to Castiel. “Just wait here for a second.”

He went back inside, leaving Castiel to stand alone in front of the closed door. Muffled voices that turned louder, then a moment of silence, and then Jo appeared at the door, hands crossed over her chest. She didn't look happy to see him.

Castiel squinted at her. “Hello.”

Jo narrowed her eyes at him. “Dean’s not here.”

“Um, do you know when-”

“No, I don’t,” she cut him off harshly. “He quit this morning,” she added quickly, her words thrown at Castiel like knives. “I’m sure you have an idea as to why.”

Castiel jerked his head back in surprise. “He quit?”

“Sure did.” Jo took a step forward, crowding in Castiel’s personal space, and despite her petite frame and their height difference, the threat in her eyes made Castiel take a step back.

“I just want to talk to him,” Castiel stammered. “Explain.”

“Yeah, Dean doesn’t want to talk to you,” Jo said. “So, get out of here.”

She turned around and slammed the door to his face with a final, “And don’t let me see you around here again.”

Dean had quit his job. And Jo apparently thought it was Castiel’s fault. Castiel hadn’t even had the chance to ask her for Dean’s address. Though he doubted she would tell him.

Castiel did the only thing that made sense. He found a bar and stayed there until he couldn’t remember his own name.

***

There was loud banging that could be inside Castiel’s head but most probably was the door. Castiel groaned. His mouth tasted like a rat had died in there and every single bone in his body hurt like he'd been thrown off a twelve-story building. Blindly he fumbled around until his hand closed around a pillow, and he pressed it over his face, hoping whoever it was that was currently murdering his door would stop and go away if he wished hard enough.

They didn’t.

They only banged harder.

“Get up, Clarence,” Meg was heard yelling over the loud noise. “I know you’re in there. Your stupid trench coat's out here on the floor.”

“Go away,” Castiel tried to say, but it came out as an incoherent mass of vowels and cries. God, he needed painkillers.

His stomach lurched, reminding him that he was not young anymore. He turned to his side, burying his head between the pillows and only then realizing he was on the couch and not in his bed.

“Come on, Clarence,” Meg yelled, and the banging became so loud Castiel started wondering if she was using her shoe to hit the door.

Finally, because his head was about to split open, he dared to crack one eye open. He immediately regretted it when a very rude sunbeam sliced straight into his brain and caused another wave of pain to travel through his body. Lovely.

Weighing his options, Castiel decided that it was far better to brave getting up and answering the door. At least all the deafening noise would stop.

Every single joint in his body crackled and popped as he slowly dragged himself up and lumbered towards the door. Yeah, definitely not young anymore.

“Fucking _finally!”_ Meg exclaimed, pushing him to the side. She dragged the trench coat with her and tossed it on the sofa, taking in Castiel’s miserable appearance. “Did someone run you over?”

Castiel grunted in reply as he fell back on the couch. A pillow landed on his face almost immediately, Meg hitting him again and again. “Get up! Jesus, Castiel. What happened to you. Did things go that badly with Dean?”

“Never found him,” Castiel muttered through clenched teeth. He lifted his hand in a half-assed attempt to protect his face but the pillow landed on him all the same.

“What do you mean you never found him? And get up,” Meg said, throwing the pillow on the floor so that she could start pulling Castiel upright again. “Go take a shower. You smell like you slept with a racoon.”

Resistance was futile. Castiel made himself get in the shower and wash as best as he could, and although his head was still thrumming like there was a philharmonic doing a concert in there, his muscles and tired bones did feel infinitely better by the time he was finished. Wearing his most comfortable pajamas, Castiel came back to the living room, where a glass of water and two aspirins were waiting for him. Castiel downed them gratefully and even finished the glass of water under Meg’s watchful eye. After he was done she pushed a grilled cheese sandwich in front of him. Castiel’s stomach complained loudly just at the sight of it, but just a glance at Meg made Castiel force the sandwich down anyway.

It was almost an hour since Meg had arrived, and although Castiel was still cranky and tired and wanted desperately to go back to sleep, he was functional. Mostly.

Meg snapped her finger in front of his eyes. “Focus.”

Castiel glared at her. “I’m trying.”

“You wouldn’t have to, if you acted like an adult,” Meg said, fetching him another glass of water. After he'd finished that, too, she added, “While you were destroying your liver last night, I actually did something useful.” She rummaged through her purse, pulling out a handful of papers and handing them over. “Contracts and papers about an offshore company. Everything is in Mrs. Brown’s name.”

“Who’s Mrs. Brown?” Castiel asked, trying to make sense of all the documents. It wasn’t easy in his current state.

“Adler’s mother,” Meg said. “Brown is her maiden name. And,” she pointed out a couple of papers on the bottom of the piles, “payments. From Holy Hosts Pharmaceuticals to the offshore. Every month like a clockwork.”

A light bulb lit inside Castiel’s mind. “Adler’s getting paid to prescribe their drugs.”

“Heavily,” Meg agreed with a nod. “And judging from the folders we went through, he doesn’t even prescribe them to patients who actually need them.”

That was it. That was the connection they'd been looking for all along. The case was as good as already won. No, it was better. This was huge. Gabriel would throw him a party when he heard.

“How did you even find this?”

Meg leaned back in her chair. “What can I say. I am that good. Did you know, there’s a doctor finishing his residency that works very closely with Adler. He isn't the most handsome boy you’ve ever seen, but he certainly loves gossip.” She raised her eyebrows at Castiel to see if he was following. “Didn’t even have to get him drunk. All I needed was a couple of hints and a rumor about a new jet ski. Once I knew what I was looking for it was easy enough to find all this.”

In all their time working together, Meg had bailed him out plenty of times, but this was without a doubt her best work. If Castiel didn’t feel nauseous just at the thought of getting up, he’d already be hugging her. “You’re a genius.”

“I know, you ought to give me a raise.”

“Anything. Anything you want.”

Meg tapped a finger against her temple. “I’ll think about it. Now, spill. What happened last night with Dean and you ended up like this.” She gestured vaguely at him with a disgusted expression.

Castiel sighed, but he told her what Jo had said and then quickly narrated the rest of the night which had been spent in a whirlwind of whiskey and beers. Briefly he wondered if he should be worried that since he’d met Dean, he seemed to be spending most of his nights _not_ sleeping and now waking up with the worst hangover of the last few years. Then he remembered that he’d also had the most fun and... well. It was worth it, even if Dean never spoke to him again.

“We’ll find him, and then you can explain,” Meg said, tapping a sympathetic hand on his shoulder. “You just get some rest today.”

“Meg, I-”

Meg shushed him immediately. “Just go to bed. Get some sleep, and we’ll figure it out after you wake up.”

As much as Castiel would have liked to argue, his brain was already half-asleep. He shuffled back in his bedroom and fell asleep as soon as his head touched the pillow. Thankfully it was much more peaceful and dreamless than last night.

***

The light had dimmed by the time Castiel returned to consciousness. How long was he asleep for? According to his alarm clock for a solid four hours. Not bad. At least the headache had lessened. He found Meg sprawled on his couch, watching Friends reruns on his TV.

“Morning, Sunshine,” she said without turning to look at him. “There’s mac n’ cheese in the fridge for you.”

Castiel raked a hand through his hair. His throat was too dry – from sleep? From the hangover? - so he shuffled in the kitchen where he waited impatiently for the food to heat in the microwave. Despite having eaten a few hours ago, he was starved, and he was surprised that the food was going down easier this time around. The mac n’ cheese didn’t taste as good as it probably had when Meg had first made it, but it warmed his insides on its way down and spread a soft, delicate sense of calm over his exhausted brain. After he was finished, he placed the empty bowl in the sink, noting that there were no other dishes to be washed. He supposed he had Meg to thank for that too.

“What’s with all the cheese?” he asked, pushing Meg’s legs to the side to sit on the couch.

“Fats are good for your hangover.”

In the screen, Rachel and Phoebe were discussing about giving Monica and Chandler more laundry to do, while Joey insisted they tell them the truth. The joke was lost on Castiel, but Meg chuckled along with the recorded audience.

“Is that another one of your Cosmo-tips?”

Meg side-eyed him before crossing her arms over her chest. “That’s from experience. I believe the Cosmo-tip would be to have another tequila shot.”

Just at the mention of alcohol Castiel’s stomach lurched. He placed a hand over it closing his eyes. “That’s terrible advice.”

Meg shrugged in a what-can-you-do motion.

Castiel sat with her for a few minutes, watching as Joey got more and more frustrated from the secret he was trying and failing to keep. Then Castiel said, “Cosmo-tips suck.”

Meg kicked him in the hip with her socked foot. “Don’t blame Cosmo for falling for an asshole.”

She was right, of course. But Castiel could still sulk like a child and not like it. He thought he'd earned it after going through the worst hangover of his life.

The episode ended, and the next one started, Meg’s eyes never leaving the screen, and soon Castiel found himself getting bored, and his eyed grew tired from the glow of the TV. He found his phone and scrolled through the photo gallery, not even caring that this light was not much better for his eyes. Most of the recent ones were photos Dean had sent him, and one photo of the burgers they had on their first fake-date. Castiel could be seen in the background. Dean had taken that picture for his brother and had sent it to Castiel after he'd complained about not having a phone to take one too. Castiel winced at the memory of the younger Winchester and the one time they had been alone for lunch. He scrolled further down, trying to force all the promises he had made that day out of his mind.

Then he paused.

His finger hovered over the screen for a second, hesitant over a familiar photo among all the others.

He pressed on it and brought it to full screen.

It was the first picture Dean had ever sent him, from the LARP event he'd attended with his friend Charlie. In the photo the two posed side by side in their costumes, wide smiles over their faces. On the bottom of the pictures Dean had drawn a few words in red.

_Queen of Moondoor_ _\+ Handmaiden._

Castiel tilted his head to the side as he considered the picture more closely.

_Queen of Moondoor. Huh._

His eyes widened, and in a rush of adrenaline he didn’t know he was capable of, he jumped off the couch and ran to his desk for his laptop.

“Hey, hey, hey,” Meg complained as she was jostled from her place. “What’s the matter with you?”

“I think I know how to find Dean.” He tapped his foot impatiently while he waited for the laptop to load and then quickly navigated to Google. Footsteps preceded Meg peering over his shoulders.

“And how’s that?”

Castiel typed ‘Queen of Moondoor’ on the search bar and hit _enter. “_ If I can just find this friend of his...” he trailed off as the results started appearing on the screen. He pressed the first link that took him to a Facebook page titled ‘Moondoor’ and he was delighted to see that it really was a LARPing group. He scrolled down until he found a picture of a familiar redhead in full costume. The tag identified her as Charlie Bradbury, Queen of Moondoor.

That was way easier than he'd expected. Kind of anticlimactic to be honest. Of course, he still had to talk with her and convince her to give up Dean’s address.

Meg elbowed him and moved closer to take a better look. “Who is she?”

“She is a friend of Dean’s. I met her once before.”

Meg squinted her eyes at the screen. She clicked on the name and navigated around her profile, which was a mix of photos from various events – most of them apparently related to comic book and movies, as far as Castiel could tell – and posts about a pair of lovebirds Charlie was apparently the owner of.

Meg nudged him. “Well, are you going to message her or what?”

Castiel hummed as he opened a chat window. He stared at it unsure for a second. The worst that could happen was that Charlie would refuse to tell him where Dean was. Or she wouldn’t answer at all. Either way Castiel didn’t have anything to lose.

_< <Hello. Is this Charlie?_

Meg rolled her eyes next to him. “Her name’s right there, genius.”

The message was read almost instantly. How lucky that Charlie would be online at exactly that moment. Castiel held his breath as three dots appeared next to Charlie’s profile picture, indicating that she was writing a reply.

>> _OMG! Cas?_

Castiel was feverish. He typed as quickly as he could.

_< <Charlie_ _I need to talk to Dean_

Castiel and Meg held their breath. The three dots appeared again but this time they were dancing on the screen for a longer time before an answer came.

>> _Can’t do. Sorry._

Castiel swallowed down his disappointment. It was a crappy plan to begin with. If Jo wouldn’t reveal Dean’s location, why would Charlie?

“We're not going down without a fight,” Meg grumbled and shoved him to the side, but before she could finish typing a new message appeared.

_> >Dean’ll_ _be hella_ _pissed if he knew I answered your message_

“She’s chatty,” Meg observed, cocking her head to the side.

“Move,” Castiel ordered and took back his place in front of the keyboard. Charlie was at least willing to hear what he had to say. Maybe. Castiel had to try either way.

_< <He’s got it all wrong_

_< <Just let me talk to him and explain_

_< <Please!_

_> >Gimme_ _one good reason_

Castiel hit send before he had fully realized what he had just written. When he did, his face flamed up, and he was sure Meg might have gasped softly, but there was no taking back his words now and even if there was, he wouldn’t. They were true, and he should have voiced them much much earlier.

_< <Because I think I’m falling for him_

There was a loud silence in the room, both from people physically and digitally present. Castiel bit his lower lip and added one more thing.

_< <Please, at least give me the chance to tell him face to face. If he doesn’t want anything to do with me after that I won’t bother him again._

The three little dots did their dance again, and it might have been Castiel projecting his own feelings and erratic heartbeat, but they looked like they were going much faster and urgently.

_> >I should block you_

Castiel’s heart fell to his feet.

>> _But adfjnsdkfhsksks_

Castiel turned to look at Meg in surprise, and she took matters in her own hand, sending back a series of question marks.

_> >I shouldn’t. Dean’s been moping around for days and he’ll barely talk to me._

_> >And do you have any idea how hard it is to hide this from Sam?_

_< <Where is he?_

_> >Cali obv_

_< <DEAN!_

_< <Charlie if you tell me where Dean is_ _I promise to let you key my car if I hurt him again_

“I’d go for ‘choke me to death with my own intestines,’” Meg observed. “But that’s just me.”

_> >I’d rather let Jo loose on you_

_< <Deal!_

_> >You promise that you want Dean to be happy_

Castiel wanted to smash his keyboard from all the frustration building up inside him. He didn’t though. Because Charlie was on the verge of giving him the information he so wanted. She was so close.

<< _Of course. I’d do anything for him_

He waited and waited and no answer came back. He stared at his screen for a good five minutes, Meg pacing behind him, but nothing changed.

“What’s taking her so long?” she asked.

“I don’t know.”

“I thought she was going to tell us.”

Castiel collapsed on the floor with his back against his desk. There was a constant buzzing in his ears and all the energy had left him. Would Charlie at least tell Dean what he'd told her? Maybe Dean would reach out to Castiel himself then, so maybe there was still a chance. Wasn’t there? Should he-

All his thoughts were cut short when there was the distinct _ting_ of a new message.

In less than a second both Meg and Castiel had their faces almost pressed to the screen. Where there was a location shared on Google maps. They exchanged a dazed look and then Meg hit her fist against the desk. “We did it!”

Castiel felt the first dainty stems of hope blooming inside him.

>> _Don’t make me regret this_

_< <I won’t_

He sent the reassurance quickly and then opened up the location. It was on the outskirts of town, maybe a half hour drive from his apartment if he was driving fast. And he was definitely going to be driving fast. He could do this.

He closed the location to find one more message from Charlie.

>> _Don’t be scared of the dog. She’s a sweetheart. Be careful_ _of Bobby’s shotgun._ 😉

Castiel read the last part twice to make sure he was reading it right. “Shotgun?”

A sweater hit him in the back of the head before he could think this any further. “Get dressed, Clarence.”


	9. Step 9: Let it go

The drive to the location Charlie had sent them passed by in a blur. Under other circumstances, Meg bouncing her leg constantly and barking orders louder than necessary – _left, left, faster, just ignore the red light and step on it –_ would have made Castiel throw her out of his car, but the adrenaline rushing through his veins made everything around him drown out in a dizzying numbness. Only one thought remained.

_Dean._

The house they arrived at wasn’t much of a house at all. It was more of a scrap yard with a bungalow squeezed among all the cars. Castiel killed the engine and stepped out of the car, Meg quickly following him. Looking through the chain-link fencing, they saw a path leading up to the front porch. Meg took a step closer and all hell broke loose.

The dog appeared out of nowhere but it – she? - looked like it was possessed with the way she jumped against the fence, teeth exposed as she barked loud enough to wake up the dead. She jumped, and she growled, and she ran from one corner of the fence to the other, glaring at them through the holes. Castiel tried to go further down, towards the door, but the dog’s barking only got louder and more threatening.

From the corner of his eyes he thought he caught movement from one of the windows up in the house. Was Dean really here? His hands were itching to do something, his feet begging him to jump over the fence and ran for his life if it meant seeing Dean again. Even if he had to go to the hospital to be treated for a dog attack after.

Meg had other plans.

She squatted close to the fence and whistled softly. The dog, still barking, focused all her attention on her, recognizing Meg as a more imminent threat to her territory. Meg stuck her hand out close enough to the fence for the dog to graze it with her teeth if she put her mind to it.

“Meg,” Castiel warned, but she shooed him away.

“I’m afraid of dogs that bite, not ones that bark.”

“How do you know she won’t bite you?”

Meg rolled her eyes, her palm still held in front of the dog. “Come on, girl,” she urged in a friendlier voice than Castiel had ever heard her use on a human being. “Don’t be afraid of little ol’ me.”

The dog quieted down but kept growling as she slowly reached her muzzle closer to the fence.

“Yes, yes,” Meg urged her on as the dog sniffed her palm through the fence and then, to Castiel’s surprise and Meg’s delight, she stuck her tongue out and licked a long streak on Meg’s palm through the fence.

“Good girl!”

The dog whined, her tail wagging enthusiastically, and then started barking again.

“This is private property.”

A man appeared at the porch, well-built but with a little roundness around his middle. He was wearing a blue cap that did nothing to hide his scowl.

Uncle Bobby, probably.

Castiel swallowed with an audible gulp. There was no shotgun in his hands from what he could see, but that didn’t mean it wasn’t waiting behind the door to be grabbed at a moment’s notice.

“Sir,” Castiel tried, because honestly, what do you call the uncle of your ex-fake-boyfriend-and-hopefully-future-real-boyfriend, who you’ve never met before? Yeah, ‘sir’ felt like the right way to go.

“Sir, please. I really need to talk to Dean.”

“Dean doesn’t want to talk to ya,” the man growled. “Didn’t think of that, did ya, idjit?”

Castiel had thought of that, actually. He just didn’t want to believe it.

“Mr. Creepy old man,” Meg said from where she was still crouched in front of the dog, and Castiel wanted to strangle her for how rude she sounded, “just five minutes of his time is all we need.”

Bobby gave her an impressive stink eye. He whistled and the dog turned around and ran back to him before they both disappeared inside the house. The discussion was clearly over, but Castiel hadn’t driven all the way out here just to leave without even seeing Dean. The dog was no longer running around the yard and now the path up to the house was clear.

Castiel opened the gate and strode up to the porch, pressing the doorbell before he could talk himself out of it.

From inside the house, the dog could be heard barking again but not right behind the door. Somewhere deeper in the house. Bobby cursed and then footsteps came up to the door.

A beat.

It wasn’t until the door handle turned that the thought he might be facing the end of a shotgun this time around occurred to Castiel, but he held his ground, planting his feet on the porch to stop them from shaking.

“Sir, please-”

“Heya, Cas,” Dean said, half of him leaning out of the door like he hadn’t decided if he wanted to come out after all. “Haven’t seen you around in a hot minute.”

Castiel frowned. His palms were sticky with sweat and his heart was beating desperately inside his chest. This was his chance. “You haven’t been answering your phone.”

Dean dropped his eyes to the ground, his ears a bright shade of red. “Yeah, uh-” He cleared his throat. “Sorry for going AWOL on you.”

“Dean, I-” Castiel started at the same time Dean said, “I just needed some space.”

They stopped and stared at each other. Dean was weary and had dark circles under his eyes. His shirt was rumpled and stained with something that could be tomato sauce, and he had a smudge on the side of his nose. Castiel was so gone on him it was drowning him, spilling out of his every pore and vibrating through his veins.

One and a half days.

That was how long he hadn’t seen and hadn’t spoken to Dean, and it was already way longer than Castiel ever wanted to spend away from him again. He lifted his arm to reach for him, but Dean froze, his fingers tight against the door frame. Castiel dropped his hand by his side.

“Let me explain.”

“’S nothing to explain,” Dean said, shrugging. “I’m happy you got what you wanted, and I’m happy for you. I really am. It’s just- you know- I-” He left his sentence unfinished, the last words lost as Castiel looked at him in confusion.

“No, Dean. Stop.”

Dean was beautiful even when exhausted and misty eyed and putting on his brave face, and all Castiel wanted to do was take him back to his apartment and keep him there until Dean knew exactly what, and most importantly _who_ Castiel wanted without a shrivel of doubt. Of course, Dean had to want the same thing first.

“This is not what I wanted. Michael is definitely not what I wanted. Not anymore, anyway,” he said, the words flooding out of him. “And you would have known that, if you hadn’t pushed me away. Again. You can’t disappear and not answer your phone without talking to me first.”

Dean gaped at him, mouth hanging open like a goldfish. “What?”

Castiel took a breath. He had already confessed to a near stranger so it shouldn’t be that hard to do it in front of the actual person. He tasted the words in his mouth and then, the whole world around him holding its breath, he said what he should have said weeks ago.

“I want you.”

Dean blinked.

“I want you, and I am here for you and I-”

Dean jumped forward, and the door sprung open, hitting Castiel on the shoulder and almost knocking him off his feet with the force of it, except Dean grabbed him and steadied him. One of Dean’s hands held on Castiel’s elbow, the other running over his shoulder in a soothing motion. The dog started shouting again from inside the house and the fence gate creaked as Meg rushed to come closer.

“Shit. Cas-”

“I’m fine, I’m fine,” he reassured him placing his own hands on Dean’s shoulders and holding on because he didn’t know what else he was supposed to do other than keep him close.

“Good,” Dean breathed out, and then they were breathing the same air for a startling second before Dean’s lips were on his and everything else faded away.

It took a second for Castiel to catch up to what was happening, but then he was kissing Dean back, desperately, his left arm behind his neck and the right coming down to drag Dean in from the front of his shirt. Dean’s hands snaked around his waist pressing them closer together from knee to chest. Castiel tilted his head. Dean chased him and deepened the kiss, tongues sliding together, first experimentally and then with more confidence. There was stubble rubbing against Castiel’s skin and firm arms around him, and it was the best kiss of his life. His mind was reeling and every molecule in his body begged for this moment to never stop, but Castiel had barely enough time to feel Dean smile against his lips before he pulled away.

The world came back into focus slowly, starting from the beautiful blush across Dean’s cheeks to the cool breeze ruffling his hair, to Meg whooping and hollering from behind him.

“You are doing amazing, Clarence!”

Tongue darting out to wet his lips, Dean agreed. “Yeah. Go, Clarence.”

They stared at each other for a moment and then Dean rubbed the back of his neck. Castiel took a step forward and brought a hand up to cup his cheek, thumb pressing small circles by the edge of his lips. Dean’s eyes widened, but he smiled softly. He cleared his throat and tapped two fingers against the back of Castiel’s hand, pointing with his eyes where Meg was standing.

“Smile for the camera, sweetcheeks,” Meg shouted, accompanied by a gruff chuckle from Bobby who had somehow manifested at the door. Meg lifted her phone higher, and Castiel, caught off guard, gave her a small wave. How long had her phone been out?

“I want that video too, missy,” Bobby declared.

Video. Okay, so the phone had been out for quite some time.

“I know someone who will throw a party once I send this to him.” A wicked smile appeared under Bobby’s beard.

Dean turned a horrified look to him. “Oh my God, Bobby. Don’t you dare send this to Sammy.”

The flush travelled lower on his face and down his neck, and Castiel went weak at the knees. Noticing the stupid expression written all over his face, Dean laced their fingers together and tugged him to the corner of the porch. Castiel went easily. At that moment he would have followed Dean to the end of the world.

“I- uh. Sorry for the audience.”

“It was a pleasure.” It truly had been. Castiel wanted to have a repeat performance as soon as possible. And he wanted a first date, a real first date this time, and he wanted Dean to come by the firm and call him babe again, and Castiel _wanted._

Dean stole a glance at Meg and Bobby who were introducing themselves and very obviously trying to eavesdrop on them. “I think we should talk. But like, somewhere more private?”

“Yes. I think that would be... wise.”

“I’ll call you?”

Castiel cocked an eyebrow. “Will you?”

“Cross my heart and hope to die.” Dean laughed. “Maybe we can have those homemade burgers I’ve promised you,” he drawled and there was a hint of _more_ laced through his words.

“I’ll bring the dessert,” Castiel promised.

Dean very deliberately eyed him from head to toe, and Castiel squirmed under the attention. “You do that.”

***

They were taking things slow. That was what Dean had said on the phone early Sunday morning, and Castiel had easily agreed. He would have agreed to anything Dean had asked after almost losing him. His priority right now, anyway, was the oncoming trial. He still had to show his opening arguments and the evidence list to Gabriel, but he felt confident with all the dirt Meg had dug up on Dr. Adler. Castiel suspected he wouldn’t be a doctor for much longer after the trial.

It was evident, by a quick look at her still empty desk, that Meg was late, which was peculiar, considering Castiel’s early morning jogging and Meg’s weird obsession with waking up at 5 a.m. to do her hair, makeup and choose the highest heels that would match her outfit, but not unheard of. After all the stress and babysitting him during the weekend, she deserved to be late. Maybe even a few days off. Castiel had to give her a couple of days off after the trial.

He made coffee, calculating that he still had at least an hour before Gabriel showed up. He still had time to run to a bakery and buy a few danishes. Gabriel would surely appreciate them. Pouring two cups of coffee, Castiel pondered if maybe he should get something with more chocolate, when Anna’s panicked voice cut all his thoughts in half.

“Meg, wait!”

God, what now?

Two cups of coffee in the same hand, Castiel opened the kitchen door and took a step outside, wondering what Meg had gotten herself into this time, only to be shoved back inside by a furious Meg as she very purposefully strode towards her target: Michael.

Leaning against the doorframe of his office, Michael smirked when he saw her and opened his mouth to say something but was cut off by her fist colliding with his nose with a sickening crunch. There was a fraction of a second where the whole office stood stunned, as Michael staggered back, clutching his bloody nose and cursing, but then Meg lifted her fist again, and at least three people, one of them Castiel, jumped in to separate them.

Meg calmed down instantly, shaking Inias’ hand off like it was filthy. She flipped her hair away from her face. “Thank you for your time, Mr. Devine,” she said, and only then did she allow Castiel to pull her away.

“What the hell, Meg?” Castiel hissed, glancing behind his shoulder at Michael who was trying to stop the bleeding with a towel somebody fetched for him.

“Karma is a bitch, Clarence,” Meg said calmly, brushing the dust off her pencil skirt. “But my fist is faster and more satisfying.”

Castiel gaped at her.

“Novak and Masters, in my office. Now.”

Chuck’s court voice boomed through the firm. It spelled trouble in all capitals and underlined three times.

Meg was acting like this was any other day at the office and they had just been invited for tea, not an ass whooping. It drove Castiel crazy that he was more upset than her.

Chuck sighed heavily, rolling a pen between his deft fingers. “I don’t want to be the bad guy-” he looked between them, biting his lower lip, “-but this is wrong on so many levels.”

Castiel remained silent, staring straight at him. Meg chose to do the same.

“You assaulted one of your co-workers,” Chuck said, voice trembling. He turned to Meg. “Give me one reason not to fire you.”

“He is an asshole.”

“You can’t hit someone because he is an asshole.”

“I just did.”

Castiel placed a hand on her knee, pleading her with his eyes to shut up. “Chuck, if you just let me explain.”

Chuck threw the pencil in his desk, raking his fingers through his hair. There was a reason Gabriel was always the one to deal with all ‘unpleasant interactions’ in the firm. Chuck did not do well with people, and he especially did not do well with scolding people. “Please, do. Because I’m trying really hard to find one mitigating circumstance, and Megan isn't helping me.”

“Just listen,” Castiel said and slowly, leaving out the whole Cosmo-plan, and fake relationship, and even his own crush on Michael, Castiel explained the situation. He stuck as close to the truth as possible, talking about how Michael had developed a sudden interest in Castiel’s cases lately and how he had tried to take first chair for the Gallagher vs Adler before Castiel asked him to keep his nose out of his business. He finally explained how Michael had followed him to the restroom back at the restaurant on Thursday and had kissed him to piss Dean off. And of course, he went into detail about Michael wanting to sabotage Castiel.

“And that’s why, although all this is in no way an excuse for how Meg acted, she was... angry enough to lash out.”

“That’s a reason for you to lash out, I don’t see you kicking Michael,” Chuck pointed out.

“One can dream,” Meg whispered, and Castiel shot her a dirty look.

“I have better self-control.”

Chuck studied them for a minute, drumming his fingers on his desk. “In light of new evidence, I’d like to take a few hours to think this over and to speak with Michael and Gabriel. Why don’t the two of you take the rest of the day off?”

“We can’t take the day off,” Castiel protested. “The trial is tomorrow, and we still have a ton of things to do.”

“Then do it in your office,” Chuck said, raising his eyebrows in warning. “Understood?”

The waiting was excruciating. Thank God Castiel and Meg really did have so much stuff to do that they couldn’t stand around biting their nails in agony. Or rather Castiel couldn’t do it, because really, Meg was as calm as ever. How could she?

“Relax, sweetcheeks,” she said after Castiel asked her. “If I get fired for standing up to that shit bag, then so be it.”

“Meg, not that what you did wasn’t amazing, but you can’t be so calm when your job is at stake.”

“So I’ll find another one,” she shrugged tracing the words on the paper she was reading.

“But what about me?” Castiel exploded. Meg lifted her eyes to look at him, a flash of sadness to her expression. “What am I going to do without you?”

She reached over and patted his hand. “Don’t worry Clarence, I’ll still take you out for drinks, and we can gossip and plot all you want.”

“I do not plot,” Castiel complained weakly.

“Oh really? And who started the Cosmo-plan that got us into this mess in the first place?”

“See? That’s why I don’t plot.”

Meg let her eyes wander his face for a few seconds, then, with a bitter smile, she said, “You’re gonna be just fine, Clarence. You’ve got all the support you need.”

But Meg wasn’t just Castiel’s support. She was his friend and his partner in crime – or rather, Castiel was her partner in crime, because Meg was the one doing all the dirty work – and the only reason Castiel was so good at his job was because Meg always had his back. She was even the reason he'd found Dean. Sorta.

When Gabriel and Chuck came knocking, they had already spoken with Michael and made their decision.

Gabriel didn't chew his words, but somehow he looked rather amused by the whole situation. “He was pissed off and wanted to sue you.”

Meg kept her head high. “Let him, my lawyer is better than him.”

Not that Castiel wasn’t flattered at her trust in him, but he could not handle this today. He could not handle any more drama, period. He needed a long relaxing month of easy to settle divorces and date nights with Dean.

“But he is not suing after all,” Chuck added.

“Cassie, you should have seen his face when I told him that you could sue him back for sexual harassment,” Gabriel said, holding back his laugh. Of course he was enjoying this. Gabriel lived and breathed for scandals and gossip, and after the latest revelations, one could imagine he wasn’t the biggest fan of Michael. Chuck on the other hand looked like he needed a vacation ASAP.

Join the club, Chuck.

Castiel hadn’t thought he could press charges against Michael. Even if he had, he'd have never done that. He was sick and tired of Michael, and if he could avoid seeing him for the foreseeable future, he would do just that.

Judging from the way Michael scrambled to hide in his office when he saw Castiel and Meg leave for the day a few hours later, he probably wasn’t in any hurry to cross paths with them either. Meg bragged it was worth it to get banned from the office for a few days if it meant Michael went pale every time he saw her. Her job was safe though. For now, as Chuck warned both of them before retreating back to his office to continue watching ant videos. His new obsession according to Meg, who heard it from Hannah.

***

Castiel was not one to brag, but the face splitting grin that was permanently etched on his face was a dead-giveaway.

The verdict was still not out, but Castiel doubted the defense could come up with anything that would save Dr. Adler. The evidence Meg had uncovered had been the turning point that had won the jury’s favour and would surely cause a much larger investigation into not only Dr. Adler and the Holy Hosts Pharmaceuticals, but two dozen more doctors whose names were heavily associated with them. Watching the opposing counsel fumble through his papers, only to realise that he had nothing to argue back and then turning to Adler who just sat there pale and trembling, Castiel felt such excitement and adrenaline rush that could only be compared to his first time stepping foot in a court.

They still had a long way to go. The defense would surely try to find some last minute evidence to at least save face, but Castiel was pretty sure victory was as good as his already.

Gallagher was ecstatic to hear he’d be getting a heavy compensation and squeezed Castiel in a bone-crushing hug before they were even out of the courthouse. He was quickly followed by Gabriel, who had come to watch the trial and support Castiel.

“I knew you’d win this, Cassie!” he yelled, kissing Castiel on both cheeks sloppily. Castiel just patted him awkwardly on the back, then followed him sheepishly back to his car to return to the firm, while Gabriel droned on and on about what a huge opportunity this was and how the press was going to be all over them once they got a sniff of the scandal. Yes, he could already see the headlines on all the major news sites, and they all should probably start getting ready to be drowned in phone calls for interviews. They had to find a second assistant for Chuck. “You know how he hates press,” Gabriel said as he jumped in the air, clapping his heels together.

Back at the firm, Castiel was congratulated by half his co-workers almost as soon as they walked in, and soon found himself in the middle of organizing a celebration for the next weekend. Thankfully, he managed to extract himself from their tight ring of questions, telling them to speak to Meg, and that she would manage everything herself. He hid in his office before anyone had time to remember that Meg was on vacation due to her... temperament.

Tuesday night came both unfairly fast and unbelievably slow. By the time Castiel managed to get back to his place, he had a little under an hour to shower and get ready, but that one hour felt like torture.

Castiel was ready in barely twenty minutes, a personal record for him.

Then he paced the floor.

He loaded the dishwasher and wiped down the counters.

Then he had to change his shirt because he got a stain on it.

Finally he parked himself by the window and watched the road anxiously.

Four minutes earlier than they had agreed, a sleek, black Impala rolled in front of his apartment building and parked.

A heartbeat. And another.

His phone chimed with a new message, and Castiel was out of the door without seeing it.

The car smelled of old leather and motor oil, mixed with a spicy scent that Castiel recognized as Dean’s aftershave.

Dean offered his hand, palm up, and a cheeky grin, and Castiel laced his fingers through Dean’s. It would be the easiest thing in the world to lean closer and kiss him, but their night hadn’t even started yet. And a first kiss – okay, their second but still – was the perfect ending to a perfect first date.

**Notes for the Chapter:**

> That's all folks!  
> I know this is not perfect but I had so much fun writing it, and I hope you all had fun reading it.
> 
> Once again I want to thank [ dmsilvisart ](https://dmsilvisart.tumblr.com/) for being the best artist I could have asked to work with on my first fic. Thank you for your beautiful illustrations and all your hard work, and thank you for answering all my questions. You rock! <3


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